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 727 946 4296.

22 Results

Oaks Osprey Florida Homes For Sale

Oaks For Sale $2,495,000

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 3 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.

Oaks For Sale $3,150,000

Luxury home nestled in a quiet neighborhood with water views at 662 Fernwalk Ln, Osprey, FL 34229
Inviting pool and spa area with screened enclosure and patio furniture at 662 Fernwalk Ln, Osprey, FL 34229
Spacious living room featuring hardwood floors and a cozy fireplace at 662 Fernwalk Ln, Osprey, FL 34229
On Market For 4 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4684

  • Year Built

    1989

  • $/SqFt

    $673

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

Oaks For Sale $2,450,000

Resort-style backyard oasis with pool, fire pit, and patio at 654 Trenton Way, Osprey, FL 34229
Inviting freeform pool and spa with covered patio and sunset views at 654 Trenton Way, Osprey, FL 34229
Relaxing fire pit area with comfortable seating in the backyard at 654 Trenton Way, Osprey, FL 34229
On Market For 13 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3582

  • Year Built

    1990

  • $/SqFt

    $684

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

Oaks For Sale $2,650,000

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 For 16 Days
  • 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

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 For 18 Days
  • 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

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 For 11 Days
  • 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

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 19 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

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 24 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 $1,874,000

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 36 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 $1,925,000

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 60 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 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
*POTENTIAL GREAT VALUE
On Market For 63 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 $2,350,000

Reduced By $150,000

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 62 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4641

  • Year Built

    2007

  • $/SqFt

    $506

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

On Market For 69 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

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 76 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

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 84 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

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 92 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

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 102 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

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 129 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

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 143 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 For Sale $1,795,000

Reduced By $100,000

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 233 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

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 279 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 Pended $3,995,000

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 318 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.

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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 727 946 4296 and speak with one of our real estate consultants.

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