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.

25 Results

Oaks Osprey Florida Homes For Sale

Oaks For Sale $2,650,000

Stunning two-story home with lush landscaping and a stately facade at 370 Sugar Mill Dr, Osprey, FL 34229
View Details 87 Photos
Inviting pool area with covered patio, outdoor kitchen, and ample seating at 370 Sugar Mill Dr, Osprey, FL 34229
Waterfront property with beautiful landscaping and a prime location at 370 Sugar Mill Dr, Osprey, FL 34229
Elegant home showcasing a manicured lawn and palm trees at 370 Sugar Mill Dr, Osprey, FL 34229
On Market Today

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4783

  • Year Built

    1996

  • $/SqFt

    $554

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. GENEROUS PROPERTY.

Oaks For Sale $1,225,000

Beautiful yellow home with lush landscaping and a large driveway at 227 Saint James Park, Osprey, FL 34229
View Details 67 Photos
Relaxing screened patio with outdoor furniture and view of lush greenery at 227 Saint James Park, Osprey, FL 34229
Aerial view of house and golf course community at 227 Saint James Park, Osprey, FL 34229
Bright yellow house with a large driveway and manicured lawn at 227 Saint James Park, Osprey, FL 34229
On Market Today

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    2071

  • Year Built

    1986

  • $/SqFt

    $592

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. GENEROUS PROPERTY.

Oaks For Sale $1,195,000

Single-story home with a light-colored exterior, a paved driveway, and lush landscaping at 32 Bayhead Ln, Osprey, FL 34229
View Details 100 Photos
An aerial view showcasing a waterfront community and a homesite with mature trees at 32 Bayhead Ln, Osprey, FL 34229
An aerial view showcasing a waterfront community and a homesite with mature trees at 32 Bayhead Ln, Osprey, FL 34229
An aerial view showcasing a waterfront community and a homesite with mature trees at 32 Bayhead Ln, Osprey, FL 34229
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2570

  • Year Built

    1993

  • $/SqFt

    $465

This home is a must see. MICHAEL SAUNDERS & COMPANY.

Oaks For Sale $2,150,000

Beautiful one-story home with lush landscaping and a large lawn at 85 Sugar Mill Dr, Osprey, FL 34229
View Details 68 Photos
Luxury home with a spacious lot and water views at 85 Sugar Mill Dr, Osprey, FL 34229
Luxury home with a large driveway and manicured landscaping at 85 Sugar Mill Dr, Osprey, FL 34229
Inviting pool and spa area with covered patio at 85 Sugar Mill Dr, Osprey, FL 34229
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    4191

  • Year Built

    1991

  • $/SqFt

    $513

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. GENEROUS PROPERTY.

Oaks For Sale $910,000

Attractive single-story home with a gray exterior, tile roof, and landscaped front yard at 293 Turquoise Ln, Osprey, FL 34229
View Details 44 Photos
Aerial view showcasing a home's location in a community with water access at 293 Turquoise Ln, Osprey, FL 34229
Single-story home with tile roof, paver driveway, and lush landscaping at 293 Turquoise Ln, Osprey, FL 34229
Bright entryway with double doors, wood-look floors, and neutral wall decor at 293 Turquoise Ln, Osprey, FL 34229
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2271

  • Year Built

    2001

  • $/SqFt

    $401

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. GENEROUS PROPERTY.

Oaks For Sale $2,000,000

Aerial view of a luxurious home with a tile roof and lush landscaping at 855 Macewen Dr, Osprey, FL 34229
View Details 100 Photos
Elegant home exterior with Mediterranean-style architecture and landscaping at 855 Macewen Dr, Osprey, FL 34229
Front view of a beautiful house featuring a three car garage and brick driveway at 855 Macewen Dr, Osprey, FL 34229
Mediterranean-style house with a brick driveway and manicured landscaping at 855 Macewen Dr, Osprey, FL 34229
On Market For 2 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4361

  • Year Built

    2006

  • $/SqFt

    $459

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

Oaks For Sale $1,874,000

Aerial view of upscale community with water features and lush landscaping at 75 Osprey Point Dr, Osprey, FL 34229
View Details 71 Photos
White two-story home with long driveway and mature landscaping at 75 Osprey Point Dr, Osprey, FL 34229
Elegant white home with black shutters and a brick driveway at 75 Osprey Point Dr, Osprey, FL 34229
Inviting pool area with patio furniture and lush landscaping at 75 Osprey Point Dr, Osprey, FL 34229
On Market For 19 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4001

  • Year Built

    1983

  • $/SqFt

    $468

Discover the unparalleled lifestyle and refined elegance of 75 Osprey Point, a home that stands apart in every detail. PREMIER SOTHEBYS INTL REALTY.

Oaks Pended $1,795,000

Light blue two-story home with tile roof, columns, and landscaped yard at 676 Eagle Watch Ln, Osprey, FL 34229
View Details 80 Photos
Light blue home with tile roof and columns at sunset at 676 Eagle Watch Ln, Osprey, FL 34229
Front entry with double doors, columns, and a tiled walkway at 676 Eagle Watch Ln, Osprey, FL 34229
Light blue home with tile roof, surrounded by shrubs and trees at 676 Eagle Watch Ln, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 30 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5399

  • Year Built

    1992

  • $/SqFt

    $332

Close to everything Sarasota County has to offer, including beaches, parks and top-ranking Pine View School. Schedule a tour today. COLDWELL BANKER REALTY.

Oaks Pended $1,925,000

Beautiful home with palm trees and a large driveway at 533 N Macewen Dr, Osprey, FL 34229
View Details 67 Photos
Luxury property nestled in a golf course community at 533 N Macewen Dr, Osprey, FL 34229
Tan house with palm trees and a long driveway at 533 N Macewen Dr, Osprey, FL 34229
Elegant entryway with double doors and ornate details at 533 N Macewen Dr, Osprey, FL 34229
On Market For 44 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3794

  • Year Built

    1999

  • $/SqFt

    $507

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

Oaks For Sale $1,825,000

Reduced By $25,000

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 For 46 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4388

  • Year Built

    1990

  • $/SqFt

    $416

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

Oaks Pended $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 52 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4641

  • Year Built

    2007

  • $/SqFt

    $539

Initiation Fees Going Up On 2/1/2025. Buy Now Before The Increase 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 53 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 60 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 68 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 76 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 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 86 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 114 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 127 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 $2,225,000

Reduced By $70,000

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 155 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3896

  • Year Built

    1989

  • $/SqFt

    $571

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

Oaks Pended $1,675,000

Reduced By $125,000

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
*POTENTIAL GREAT VALUE
On Market For 205 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4614

  • Year Built

    2003

  • $/SqFt

    $363

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

Oaks For Sale $1,795,000

Reduced By $100,000

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 217 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3464

  • Year Built

    2014

  • $/SqFt

    $518

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
On Market For 263 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 302 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 302 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 Pended $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 252 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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