Below you can view all the homes for sale in the Oaks subdivision located in Osprey Florida. Listings in Oaks are updated daily from data we receive from the Tampa multiple listing service.

To learn more about any of these homes or to receive custom notifications when a new property is listed for sale in Oaks, give us a call at 813-527-9259.

18 Results

Oaks Osprey Florida Homes For Sale

Oaks For Sale $1,850,000

Two-story house with tile roof, fountain, and lush landscaping at 401 Walls Way, Osprey, FL 34229
View Details 92 Photos
Two-story house with tile roof, fountain, and lush landscaping at sunset at 401 Walls Way, Osprey, FL 34229
Front entry of two-story house with tile roof and walkway at 401 Walls Way, Osprey, FL 34229
Two-story house with tile roof and circular driveway at 401 Walls Way, Osprey, FL 34229
On Market Today

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4388

  • Year Built

    1990

  • $/SqFt

    $422

Don’t miss this opportunity to bring your most discerning clients to experience this extraordinary home. RE/MAX ALLIANCE GROUP.

Oaks For Sale $2,500,000

Luxury home with circular driveway, lush landscaping, and three-car garage at 703 Macewen Dr, Osprey, FL 34229
View Details 100 Photos
Impressive home showcasing a grand entrance and manicured landscaping at 703 Macewen Dr, Osprey, FL 34229
Elegant home exterior featuring a three-car garage and beautiful landscaping at 703 Macewen Dr, Osprey, FL 34229
Luxury home with a three-car garage and meticulously landscaped grounds at 703 Macewen Dr, Osprey, FL 34229
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4641

  • Year Built

    2007

  • $/SqFt

    $539

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. COLDWELL BANKER REALTY.

Oaks Pended $1,500,000

Beautiful home with lush landscaping and mature trees at 378 Macewen Dr, Osprey, FL 34229
View Details 1 Photo
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3094

  • Year Built

    1997

  • $/SqFt

    $485

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

Oaks For Sale $959,000

Single-story house with landscaped yard, palm trees, and a brick driveway at 21 Bayhead Ln, Osprey, FL 34229
View Details 92 Photos
Bird's-eye view of a house and surrounding neighborhood, near the water at 21 Bayhead Ln, Osprey, FL 34229
Property showcasing a tile roof, and a lush green lawn at 21 Bayhead Ln, Osprey, FL 34229
House with tile roof and driveway, surrounded by trees and landscaping at 21 Bayhead Ln, Osprey, FL 34229
On Market For 14 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. MICHAEL SAUNDERS & COMPANY.

Oaks For Sale $950,000

Attractive single-story home with yellow garage door and paver driveway, surrounded by lush landscaping at 186 Turquoise Ln, Osprey, FL 34229
View Details 90 Photos
House exterior featuring a yellow two-car garage, paver driveway, and palm trees at 186 Turquoise Ln, Osprey, FL 34229
Front view of a single-story house with a yellow garage door and a well-maintained lawn at 186 Turquoise Ln, Osprey, FL 34229
Single story house with yellow painted exterior, two-car garage and mature landscaping at 186 Turquoise Ln, Osprey, FL 34229
On Market For 23 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. COLDWELL BANKER REALTY.

Oaks For Sale $4,495,000

Grand two-story home with circular drive and fountain at 854 Macewen Dr, Osprey, FL 34229
View Details 82 Photos
Expansive pool and patio area with fire pit and outdoor kitchen at 854 Macewen Dr, Osprey, FL 34229
Large home with three-car garage and manicured landscaping at 854 Macewen Dr, Osprey, FL 34229
Spacious living room with a modern fireplace and pool view at 854 Macewen Dr, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 31 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** GENEROUS PROPERTY.

Oaks Pended $1,295,000

Two-story house with driveway and landscaped yard at 219 Saint James Park, Osprey, FL 34229
View Details 72 Photos
House exterior, two-story, with tile roof and landscaping at 219 Saint James Park, Osprey, FL 34229
Two story house with tile roof and lush landscaping at 219 Saint James Park, Osprey, FL 34229
Front porch with double doors and seating area at 219 Saint James Park, Osprey, FL 34229
On Market For 32 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** GENEROUS PROPERTY.

Oaks For Sale $1,690,000

Gray two-story home with a blue door and paver driveway at 325 Osprey Point Dr, Osprey, FL 34229
View Details 54 Photos
House nestled in a waterfront community with lush landscaping at 325 Osprey Point Dr, Osprey, FL 34229
Gray home with a paver driveway and landscaping at dusk at 325 Osprey Point Dr, Osprey, FL 34229
Peaceful waterfront scene with a vibrant sunset reflection at 325 Osprey Point Dr, Osprey, FL 34229
On Market For 41 Days

  • Bedrooms

    3

  • Full Bath(s)

    4

  • Sq. Ft.

    3905

  • Year Built

    1986

  • $/SqFt

    $433

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

Oaks For Sale $925,000

Single-story home with two-car garage and lush landscaping at 13 Bayhead Ln, Osprey, FL 34229
View Details 100 Photos
Bird's eye view of single-story home with pool and lush surroundings at 13 Bayhead Ln, Osprey, FL 34229
Aerial view showcasing home near the waterfront in a tranquil community at 13 Bayhead Ln, Osprey, FL 34229
Single-story home nestled in a wooded area with a large yard at 13 Bayhead Ln, Osprey, FL 34229
On Market For 69 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. MICHAEL SAUNDERS & COMPANY.

Oaks For Sale $1,795,000

Luxury home with tile roof and circular driveway, aerial view at 909 Macewen Dr, Osprey, FL 34229
View Details 62 Photos
Mediterranean style home with palm trees and circular driveway at 909 Macewen Dr, Osprey, FL 34229
Screened pool and spa with brick pavers and covered patio area at 909 Macewen Dr, Osprey, FL 34229
Elegant home with double doors and circular driveway at 909 Macewen Dr, Osprey, FL 34229
On Market For 82 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    4241

  • Year Built

    1991

  • $/SqFt

    $423

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

Oaks Pended $2,599,000

Home exterior with walkway and landscaping at 425 E Macewen Dr, Osprey, FL 34229
View Details 96 Photos
Pathway through lush landscaping leading to home entrance at 425 E Macewen Dr, Osprey, FL 34229
Elegant double front doors with iron accents at 425 E Macewen Dr, Osprey, FL 34229
Open living room with hardwood floors and views at 425 E Macewen Dr, Osprey, FL 34229
On Market For 92 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5153

  • Year Built

    1999

  • $/SqFt

    $504

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

Oaks Pended $2,295,000

Luxury home exterior with lush landscaping and driveway at 627 Eagle Watch Ln, Osprey, FL 34229
View Details 63 Photos
Aerial view of luxury home near water and golf course at 627 Eagle Watch Ln, Osprey, FL 34229
Luxury home exterior with paver driveway and garage at 627 Eagle Watch Ln, Osprey, FL 34229
Luxury home exterior with paver driveway and entryway at 627 Eagle Watch Ln, Osprey, FL 34229
On Market For 113 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** GENEROUS PROPERTY.

Oaks For Sale $1,725,000

Reduced By $75,000

Luxury estate home with red tile roof and lush landscaping at 738 Macewen Dr, Osprey, FL 34229
View Details 100 Photos
Two-story house with red tile roof, lush landscaping, and a brick driveway at 738 Macewen Dr, Osprey, FL 34229
Two-story house with red tile roof, lush landscaping, and a brick driveway at 738 Macewen Dr, Osprey, FL 34229
Two-story house with red tile roof, lush landscaping, and a brick driveway at 738 Macewen Dr, Osprey, FL 34229
On Market For 160 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! COLDWELL BANKER REALTY.

Oaks For Sale $1,875,000

Reduced By $20,000

Beautiful house exterior with three-car garage and landscaping at 402 Walls Way, Osprey, FL 34229
View Details 58 Photos
Aerial view of a house on a golf course with a pool at 402 Walls Way, Osprey, FL 34229
Bird's-eye view of a rectangular pool with spa and patio area at 402 Walls Way, Osprey, FL 34229
Single-story home with palm trees and manicured lawn at 402 Walls Way, Osprey, FL 34229
On Market For 172 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** GENEROUS PROPERTY.

Oaks For Sale $1,800,000

Reduced By $300,000

Luxury home with circular driveway, surrounded by lush landscaping at 97 Sugar Mill Dr, Osprey, FL 34229
View Details 89 Photos
Grand two-story home, gray exterior, gray roof, lush landscaping at 97 Sugar Mill Dr, Osprey, FL 34229
Two-story home with pool and lush landscaping. Gray exterior and roof at 97 Sugar Mill Dr, Osprey, FL 34229
Two-story home with a double door entry and lush landscaping at 97 Sugar Mill Dr, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 218 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! ! COLDWELL BANKER REALTY.

Oaks For Sale $995,000

Beautiful house exterior with lush landscaping and paver driveway at 12 Bishops Court Rd Rd, Osprey, FL 34229
View Details 76 Photos
Elegant house entrance with double doors and lush landscaping at 12 Bishops Court Rd Rd, Osprey, FL 34229
Single-Gathering home with paver driveway and tropical landscaping at 12 Bishops Court Rd Rd, Osprey, FL 34229
The Oaks Preserve entrance with landscaping and signage at 12 Bishops Court Rd Rd, Osprey, FL 34229
On Market For 257 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. MICHAEL SAUNDERS & COMPANY.

Oaks Pended $3,995,000

Luxury home with a modern design, featuring a paved walkway and manicured landscaping at 601 Fernwalk Ln, Osprey, FL 34229
View Details 81 Photos
Luxury home with modern architecture, landscaped grounds, and a paved driveway at 601 Fernwalk Ln, Osprey, FL 34229
Aerial view of a house nestled in lush greenery, near the water at 601 Fernwalk Ln, Osprey, FL 34229
Luxury home showcasing a large lot with mature trees and a paved driveway at 601 Fernwalk Ln, Osprey, FL 34229
On Market For 257 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    5453

  • Year Built

    1986

  • $/SqFt

    $733

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

Oaks For Sale $999,000

Reduced By $96,000

One-story home with tile roof and large oak tree at 201 Saint James Park, Osprey, FL 34229
View Details 69 Photos
One-story home with tile roof and driveway at 201 Saint James Park, Osprey, FL 34229
Home entrance with double doors and arched entryway at 201 Saint James Park, Osprey, FL 34229
Spacious living room with large windows and glass doors at 201 Saint James Park, Osprey, FL 34229
On Market For 209 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2855

  • Year Built

    1997

  • $/SqFt

    $350

Make this your dream home in Paradise. SUBSTANCIAL PRICE IMPROVEMENT! ROSEBAY INTERNATIONAL REALTY, INC.

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Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 813-527-9259 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Anna Maria
$4,304,583
$3,350,000
30
0.0%
36.7%
150

Bradenton
$747,395
$585,000
1303
0.8%
51.9%
95

Bradenton Beach
$2,830,660
$2,999,000
11
0.0%
72.7%
237

Cortez
$1,244,000
$1,450,000
11
0.0%
18.2%
67

Ellenton
$544,545
$535,000
31
0.0%
48.4%
106

Englewood
$614,941
$450,000
411
0.5%
47.4%
97

Holmes Beach
$2,913,067
$1,450,000
45
0.0%
35.6%
111

Lakewood Ranch
$1,119,837
$825,000
276
0.4%
53.6%
98

Longboat Key
$5,092,999
$3,395,000
57
1.8%
26.3%
109

Myakka City
$1,107,913
$750,000
37
0.0%
48.6%
120

Nokomis
$826,324
$591,025
302
0.7%
53.0%
107

North Port
$390,639
$365,000
1011
1.1%
51.3%
124

Palmetto
$497,561
$414,995
374
0.8%
53.5%
85

Parrish
$522,783
$449,884
787
0.6%
55.8%
94

Sarasota
$1,313,616
$689,000
1491
0.5%
46.5%
97

Terra Ceia
$1,498,271
$1,395,000
7
0.0%
28.6%
66

Venice
$586,028
$519,990
805
0.2%
49.7%
99

EasyStreet

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