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 727 776 3277.

26 Results

Oaks Osprey Florida Homes For Sale

Oaks For Sale $1,299,000

Beautiful home exterior with mature landscaping, a brick driveway and an attached three-car garage at 223 Saint James Park, Osprey, FL 34229
Inviting front porch featuring classic columns, brick flooring, and an elegant front door at 223 Saint James Park, Osprey, FL 34229
Spacious covered porch with brick flooring and views of manicured landscaping at 223 Saint James Park, Osprey, FL 34229
On Market For 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3321

  • Year Built

    1991

  • $/SqFt

    $391

The Oaks is proud to be a Platinum Club of America and holds a renowned 5-Star rating. RE/MAX ALLIANCE GROUP.

Oaks For Sale $2,395,000

Elegant front entryway with arched windows and double doors flanked by white columns at 600 Eagle Watch Ln, Osprey, FL 34229
Bright foyer featuring double doors with decorative glass and light hardwood floors at 600 Eagle Watch Ln, Osprey, FL 34229
Sunlit bedroom with hardwood floors, wood shuttered windows and crown molding at 600 Eagle Watch Ln, Osprey, FL 34229
On Market For 7 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3681

  • Year Built

    1992

  • $/SqFt

    $651

This is a rare chance to step into a like-new home on one of the premier lots in Southwest Sarasota’s most established and visually striking neighborhoods. COLDWELL BANKER REALTY.

Oaks For Sale $2,500,000

Close-up view of a home's entrance featuring columns, a double door, manicured shrubs and landscaping at 340 Osprey Point Dr, Osprey, FL 34229
Inviting living room with a large white sectional, custom cabinets, and an open floor plan at 340 Osprey Point Dr, Osprey, FL 34229
Open-concept living space with a fireplace, a TV, and custom cabinets with a beverage bar at 340 Osprey Point Dr, Osprey, FL 34229
On Market For 10 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    6001

  • Year Built

    1998

  • $/SqFt

    $417

Don’t miss your chance to own this exceptional estate—schedule your private tour today and experience the luxury of life at The Oaks Bayside. RE/MAX ALLIANCE GROUP.

Oaks For Sale $965,000

Relaxing pool area with screened enclosure offering serene views of nature at 13 Bayhead Ln, Osprey, FL 34229
Bright, all-white kitchen with marble countertops and tiled floor at 13 Bayhead Ln, Osprey, FL 34229
Elegant bathroom with double vanity, granite countertop and a walk-in shower at 13 Bayhead Ln, Osprey, FL 34229
On Market For 12 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    2310

  • Year Built

    2001

  • $/SqFt

    $418

**PLEASE ENJOY VIEWING the 3D VIRTUAL TOUR** GENEROUS PROPERTY.

Oaks For Sale $2,900,000

Tranquil backyard featuring a private pool, spa, and an outdoor dining area perfect for entertaining at 236 Saint James Park, Osprey, FL 34229
Elegant foyer with marble floors, a grand chandelier, and a view of the staircase at 236 Saint James Park, Osprey, FL 34229
Spacious main bedroom with a four-poster bed, sitting area, and large windows with natural light at 236 Saint James Park, Osprey, FL 34229
On Market For 19 Days
  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    6246

  • Year Built

    1986

  • $/SqFt

    $464

Membership at The Oaks is required. MICHAEL SAUNDERS & COMPANY.

Oaks Pended $1,800,000

Elegant two-story home with a symmetrical facade, well-maintained lawn and mature trees at 916 Macewen Dr, Osprey, FL 34229
Close-up of the home's front entrance featuring double doors, sidelights and stately columns at 916 Macewen Dr, Osprey, FL 34229
A grand foyer with a staircase, chandelier, high ceilings, and marble floors at 916 Macewen Dr, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 7 Days
  • Bedrooms

    5

  • Full Bath(s)

    7

  • Sq. Ft.

    5987

  • Year Built

    1991

  • $/SqFt

    $301

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 of social events, The Oaks is truly Sarasota’s premier golf and country club. COLDWELL BANKER REALTY.

Oaks For Sale $1,695,000

Beautiful home featuring a brick driveway and an attached three-car garage at 402 Walls Way, Osprey, FL 34229
Covered outdoor living space featuring brick flooring, ceiling fans, and an inviting ambiance at 402 Walls Way, Osprey, FL 34229
Inviting outdoor patio features brick pavers, a dining area, and a view of the pool surrounded by lush landscaping at 402 Walls Way, Osprey, FL 34229
On Market For 26 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3464

  • Year Built

    2014

  • $/SqFt

    $489

Situated in the heart of South Sarasota, The Oaks Club is home to 2 championship golf courses, has a world class tennis program, a state-of-the-art WellFit center, exceptional dining options, and a myriad of recreational and social activities. COLDWELL BANKER REALTY.

Oaks For Sale $2,795,000

Reduced By $200,000

Elegant home featuring manicured landscaping, a neutral facade, and a welcoming entrance at 49 Osprey Point Dr, Osprey, FL 34229
Beautiful home featuring a stone walkway leading to a striking entryway and modern design at 49 Osprey Point Dr, Osprey, FL 34229
Zen courtyard with stone fountain, pebble ground cover, and serene views through floor to ceiling windows at 49 Osprey Point Dr, Osprey, FL 34229
On Market For 41 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3953

  • Year Built

    1989

  • $/SqFt

    $707

At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance. MICHAEL SAUNDERS & COMPANY.

Oaks For Sale $1,625,000

Reduced By $50,000

Aerial shot of the pool area, showcasing screened-in pool, patio furniture and serene backyard pond at 20 Bayhead Ln, Osprey, FL 34229
Expansive aerial perspective of the property, highlighting its position near a tranquil pond and surrounding greenery at 20 Bayhead Ln, Osprey, FL 34229
Overhead view showcasing the home's location, complete with a pond, mature trees, and neighboring residences at 20 Bayhead Ln, Osprey, FL 34229
On Market For 52 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3486

  • Year Built

    2017

  • $/SqFt

    $466

Don’t miss this opportunity to own a piece of paradise—schedule your private tour today! SARASOTA LAND AND HOMES LLC.

Oaks For Sale $1,995,000

Charming one-story home features arched windows, a red door, and well-manicured landscaping at 67 Sugar Mill Dr, Osprey, FL 34229
Overhead view of the home with screened lanai, nestled amidst lush trees and greenery at 67 Sugar Mill Dr, Osprey, FL 34229
A captivating aerial view shows a neighborhood with a lake and ocean in the distance at 67 Sugar Mill Dr, Osprey, FL 34229
On Market For 54 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4020

  • Year Built

    1989

  • $/SqFt

    $496

The furniture in the home is from a staging company and is not owned by the seller and not for sale MAPP REALTY & INVESTMENT CO.

Oaks For Sale $1,700,000

Impressive two-story home with a grand entrance and manicured landscaping at 282 Shell Midden Ct, Osprey, FL 34229
Elegant home with a three-car garage and inviting walkway at 282 Shell Midden Ct, Osprey, FL 34229
Stunning home showcasing a spacious driveway and lush landscaping at 282 Shell Midden Ct, Osprey, FL 34229
On Market For 71 Days
  • Bedrooms

    3

  • Full Bath(s)

    4

  • Sq. Ft.

    3699

  • Year Built

    1992

  • $/SqFt

    $460

Club membership is required with homeownership. COLDWELL BANKER REALTY.

Oaks Pended $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 67 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 $2,995,000

Reduced By $155,000

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 75 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4359

  • Year Built

    1989

  • $/SqFt

    $687

**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 83 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
Beautiful home showcasing tropical landscaping, circular drive and covered front entry at 370 Sugar Mill Dr, Osprey, FL 34229
On Market For 87 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 Pended $1,095,000

Reduced By $100,000

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 81 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2570

  • Year Built

    1993

  • $/SqFt

    $426

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

Oaks For Sale $1,045,000

Reduced By $180,000

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 88 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    2071

  • Year Built

    1986

  • $/SqFt

    $505

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

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 90 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 95 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 $1,649,000

Reduced By $225,000

Charming home with symmetrical design, elegant landscaping, and decorative exterior lighting at 75 Osprey Point Dr, Osprey, FL 34229
Expansive estate with lush greenery, sparkling pool, and architectural roofline at twilight at 75 Osprey Point Dr, Osprey, FL 34229
An aerial view showcasing a lush community, scenic water views, and beautiful residential properties at 75 Osprey Point Dr, Osprey, FL 34229
On Market For 107 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4001

  • Year Built

    1983

  • $/SqFt

    $412

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

Oaks For Sale $1,825,000

Reduced By $25,000

Charming front entrance with brick walkway and well-maintained tropical landscaping at 401 Walls Way, Osprey, FL 34229
Charming exterior elevation with a large, well-manicured lawn and a long driveway at 401 Walls Way, Osprey, FL 34229
Inviting foyer with hardwood floors, a decorative mirror, and a grand double-door entry at 401 Walls Way, Osprey, FL 34229
On Market For 134 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 $1,500,000

On Market For 140 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 147 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 $4,195,000

Reduced By $300,000

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 163 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    9081

  • Year Built

    2003

  • $/SqFt

    $462

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

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 214 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 $1,800,000

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
On Market For 350 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.

  • 1
EasyStreet

Call to Schedule a Showing

(727) 776-3277

(727) 776-3277