Market Snapshot of Listings in oaks - Osprey, FL 34229
The current prices for all Real Estate Listings in oaks - Osprey, FL are reflected in the the table below.

Market Snapshot

Averages based on current search criteria as of 06/12/2026 3:39 AM

Class Total Price Beds Baths Age
Residential 23 $1,066,774 2.7 2.3 36.1
Vacant Land 2 $697,000 - - -
Displaying results 11-20 of 26
70 Photos 156 Bishops Court Road Osprey, FL 34229

156 Bishops Court Road
Osprey, FL 34229
Oaks
Residential

MLS# A4691664 / Active
3 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 3112 Sqft
Area: 34229 - Osprey, Subdivision: Oaks

One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless residence is privately positioned ... 

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$1,289,000
Provided courtesy of DOUGLAS ELLIMAN
70 Photos 51 Macewen Drive UNIT #12 Osprey, FL 34229

51 Macewen Drive UNIT #12
Osprey, FL 34229
Oaks
Residential

MLS# A4690540 / Active
1 Beds, 1.00 Total Baths, 1 Full Bath, 623 Sqft
Area: 34229 - Osprey, Subdivision: Oaks

Situated in Windsor Lodge in The Oaks Clubside, this updated second floor condo has a kitchenette with quartz countertops, a modern bath, a bonus s... 

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$275,000
Provided courtesy of COLDWELL BANKER REALTY
19 Photos 51 Mac Ewen Drive UNIT #14 Osprey, FL 34229

51 Mac Ewen Drive UNIT #14
Osprey, FL 34229
Oaks
Residential

MLS# A4690371 / Active
1 Beds, 1.00 Total Baths, 1 Full Bath, 595 Sqft
Area: 34229 - Osprey, Subdivision: Oaks

This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-lin... 

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$285,000
Provided courtesy of COLDWELL BANKER REALTY
70 Photos 402 Macewen Drive Osprey, FL 34229

402 Macewen Drive
Osprey, FL 34229
Oaks
Residential

MLS# A4690018 / Active
3 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 3565 Sqft
Area: 34229 - Osprey, Subdivision: Oaks

Tucked behind the private gates of The Oaks Club side, in one of Sarasotas most prestigious and sought-after country club enclaves, this exquisite ... 

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$1,699,000
Reduced -$51,000
Provided courtesy of COLDWELL BANKER REALTY
52 Photos 448 E Macewen Drive Osprey, FL 34229

448 E Macewen Drive
Osprey, FL 34229
Oaks
Residential

MLS# A4687195 / Active
4 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 3768 Sqft
Area: 34229 - Osprey, Subdivision: Oaks

**IMPRESSIVE GOLF COURSE ESTATE IN THE HIGHLY SOUGHT-AFTER OAKS COUNTRY CLUB** Situated on an oversized 0.59-acre lot, this exceptional, meticulous... 

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$2,100,000
Provided courtesy of GENEROUS PROPERTY
70 Photos 61 Bayhead Lane Osprey, FL 34229

61 Bayhead Lane
Osprey, FL 34229
Oaks
Residential

MLS# A4685559 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 3180 Sqft
Area: 34229 - Osprey, Subdivision: Oaks

Thoughtfully Built MAINTENANCE-FREE Court Yard Life Style Home in Bishops Court in the Oaks Preserve Neighborhood. This Rare Unique Home Design Fea... 

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$1,185,000
Provided courtesy of RE/MAX ALLIANCE GROUP
70 Photos 57 Bishops Court Road UNIT #121 Osprey, FL 34229

57 Bishops Court Road UNIT #121
Osprey, FL 34229
Oaks
Residential

MLS# A4680582 / Active
2 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 1890 Sqft
Area: 34229 - Osprey, Subdivision: Oaks

Enjoy the perfect maintenance free country club lifestyle in the charming and quaint Bishopscourt Townhomes located in The Oaks Preserve. Architect... 

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$655,000
Reduced -$30,000
Provided courtesy of MICHAEL SAUNDERS & COMPANY
1 Photos 410 Blue Garden Lane Osprey, FL 34229

410 Blue Garden Lane
Osprey, FL 34229
Oaks
Vacant Land

MLS# A4679677 / Active

Exceptional opportunity to build your dream estate in The Oaks, one of South Sarasotas most prestigious gated golf and country club communities. Si... 

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$699,000
Provided courtesy of ELITE PROPERTIES LLC
69 Photos 33 Bishops Court Road UNIT #118 Osprey, FL 34229

33 Bishops Court Road UNIT #118
Osprey, FL 34229
Oaks
Residential

MLS# A4678425 / Active
2 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 1890 Sqft
Area: 34229 - Osprey, Subdivision: Oaks

**EXPERIENCE EFFORTLESS LIVING in this BEAUTIFULLY UPDATED TOWNHOUSE with SERENE WATER VIEWS** Located behind the Secure Gates of The Oaks Preserve... 

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$679,000
Reduced -$18,500
Provided courtesy of GENEROUS PROPERTY
70 Photos 25 Sugar Mill Drive Osprey, FL 34229

25 Sugar Mill Drive
Osprey, FL 34229
Oaks
Residential

MLS# A4678423 / Active
3 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 3066 Sqft
Area: 34229 - Osprey, Subdivision: Oaks

METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESER... 

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$1,489,000
Reduced -$61,000
Provided courtesy of GENEROUS PROPERTY

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