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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 941-445-3138.

18 Results

Oaks Osprey Florida Homes For Sale

Oaks For Sale $3,900,000

Stunning waterfront home with lush landscaping, beautiful water views, and a grand, columned entrance at 112 Osprey Point Dr, Osprey, FL 34229
View Details 76 Photos
Elegant estate with stately columns, a private balcony, and meticulously manicured landscaping at 112 Osprey Point Dr, Osprey, FL 34229
Waterfront estate with an amazing water view, lush landscaping, and a serene pond nearby at 112 Osprey Point Dr, Osprey, FL 34229
Aerial view of waterfront estate with beautiful landscaping, private dock, and access to open water at 112 Osprey Point Dr, Osprey, FL 34229
*IS BANK OWNED
On Market For 33 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    8635

  • Year Built

    1989

  • $/SqFt

    $452

This exceptional property is ready for your private tour at your convenience. KARA MONEY LLC.

Oaks For Sale $1,595,000

Charming one story home with brick driveway, lush green yard, and mature trees at 228 Saint James Park, Osprey, FL 34229
View Details 100 Photos
Aerial view of home on the golf course near the water, with serene landscaping at 228 Saint James Park, Osprey, FL 34229
Beautiful aerial view of home on golf course, surrounded by lush landscaping and water views at 228 Saint James Park, Osprey, FL 34229
Beautiful aerial view of home, with enclosed pool, near the water and surrounded by golf course at 228 Saint James Park, Osprey, FL 34229
On Market For 49 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2425

  • Year Built

    1997

  • $/SqFt

    $658

And The Oaks Club has been designated a Platinum Club of America and an Emerald Club, signifying its standing among the finest country clubs in Florida and the nation. Schedule a showing today! MICHAEL SAUNDERS & COMPANY.

Oaks For Sale $2,390,000

Reduced By $5,000

Beautiful single-story home with lush landscaping, mature shade trees, and a circular driveway at 600 Eagle Watch Ln, Osprey, FL 34229
View Details 85 Photos
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 59 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3681

  • Year Built

    1992

  • $/SqFt

    $649

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

Elegant two-story home featuring a lush green lawn, manicured landscaping, and a stately entrance at 340 Osprey Point Dr, Osprey, FL 34229
View Details 72 Photos
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
*POTENTIAL GREAT VALUE
On Market For 62 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

Charming home featuring a paved driveway, manicured landscaping, and exterior lighting at 13 Bayhead Ln, Osprey, FL 34229
View Details 62 Photos
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 64 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

Stately home with lush landscaping, circular drive, and elegant architectural details at twilight at 236 Saint James Park, Osprey, FL 34229
View Details 88 Photos
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 71 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 For Sale $1,650,000

Reduced By $45,000

Stunning home with a tile roof, paver driveway, lush landscaping, and serene water views at 402 Walls Way, Osprey, FL 34229
View Details 79 Photos
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 78 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3464

  • Year Built

    2014

  • $/SqFt

    $476

Let me know if you’d like a shorter version for MLS or social media, or if you want a more casual tone for marketing materials! COLDWELL BANKER REALTY.

Oaks For Sale $2,795,000

Reduced By $200,000

Stunning home exterior featuring lush landscaping, elegant design, and inviting entrance at 49 Osprey Point Dr, Osprey, FL 34229
View Details 95 Photos
Bright living room with high ceilings, fireplace, and comfortable seating areas at 49 Osprey Point Dr, Osprey, FL 34229
Spacious living room with stylish decor, modern design, and comfortable seating 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 93 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 $1,995,000

Elegant home showcasing a circular paver driveway, lush landscaping, and a three-car garage at 67 Sugar Mill Dr, Osprey, FL 34229
View Details 93 Photos
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 106 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 $1,600,000

Reduced By $100,000

Aerial view of a luxurious home nestled in a waterfront community at 282 Shell Midden Ct, Osprey, FL 34229
View Details 100 Photos
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 123 Days

  • Bedrooms

    3

  • Full Bath(s)

    4

  • Sq. Ft.

    3699

  • Year Built

    1992

  • $/SqFt

    $433

Club membership is required with homeownership. COLDWELL BANKER REALTY.

Oaks For Sale $2,995,000

Reduced By $155,000

Beautiful 1-story home with a tile roof and lush landscaping at 662 Fernwalk Ln, Osprey, FL 34229
View Details 80 Photos
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 127 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 Pended $2,450,000

Luxury home with pool and lush landscaping on a golf course at 654 Trenton Way, Osprey, FL 34229
View Details 85 Photos
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 136 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 $1,045,000

Reduced By $180,000

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 For 141 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

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 142 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 147 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 $1,825,000

Reduced By $25,000

Stunning two-story home boasts lush landscaping, a red tile roof, and a circular driveway at 401 Walls Way, Osprey, FL 34229
View Details 89 Photos
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 185 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 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 199 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 $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 266 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.

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Viewing HOMES 1 to 18 of 18

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 941-445-3138 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Anna Maria
$3,796,274
$2,995,000
78
0.0%
46.2%
114

Bradenton
$737,689
$599,000
1619
0.6%
58.5%
91

Bradenton Beach
$3,517,830
$2,999,000
30
0.0%
63.3%
145

Cortez
$1,445,270
$1,544,500
20
0.0%
45.0%
92

Ellenton
$554,088
$509,950
52
0.0%
65.4%
73

Englewood
$665,491
$469,000
621
1.0%
61.8%
112

Holmes Beach
$2,781,570
$1,850,000
128
0.0%
55.5%
101

Lakewood Ranch
$972,773
$699,000
432
0.0%
66.7%
108

Longboat Key
$4,039,162
$2,399,500
129
0.8%
54.3%
134

Myakka City
$1,499,489
$1,125,000
36
0.0%
55.6%
120

Nokomis
$1,078,851
$599,000
403
0.5%
71.5%
121

North Port
$381,311
$359,000
1103
1.0%
60.9%
125

Palmetto
$574,824
$415,000
407
1.0%
63.4%
79

Parrish
$511,829
$445,050
929
0.8%
60.7%
92

Sarasota
$1,442,982
$750,000
2064
0.3%
59.0%
98

Terra Ceia
$1,520,431
$1,072,500
16
6.2%
68.8%
110

Venice
$585,926
$497,290
1037
0.5%
68.4%
113

EasyStreet

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