Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed floor plan with expansive living areas, soaring ceilings, and an abundance of natural light. At the heart of the home is a completely renovated chef’s kitchen, featuring high-end finishes, premium appliances, custom cabinetry, and a seamless flow into the main living and entertaining spaces, perfect for both everyday living and hosting guests in style. Each of the five spacious bedrooms offers comfort and privacy, while the six bathrooms provide ample convenience for family and guests. Recent updates include a brand-new roof, and renovated kitchen, offering peace of mind and long-term value for the next owner. Outdoor living is equally impressive, with tranquil surroundings that capture the essence of Florida living, ideal for relaxing, entertaining, or simply enjoying the natural beauty that defines The Oaks Bayside.
Residents enjoy access to The Oaks Club, a private, member-owned country club offering championship golf, tennis, fitness, dining, and a vibrant social lifestyle. Conveniently located near top-rated schools, beaches, dining, and shopping, this home delivers the perfect balance of privacy and accessibility.
Experience refined living in one of the area’s most sought after communities, this is more than a home, it’s a lifestyle.
Residents enjoy access to The Oaks Club, a private, member-owned country club offering championship golf, tennis, fitness, dining, and a vibrant social lifestyle. Conveniently located near top-rated schools, beaches, dining, and shopping, this home delivers the perfect balance of privacy and accessibility.
Experience refined living in one of the area’s most sought after communities, this is more than a home, it’s a lifestyle.
Property Details
Price:
$1,950,000
MLS #:
A4691789
Status:
Active
Beds:
5
Baths:
5.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
OAKS
Neighborhood:
34229osprey
Listed Date:
May 1, 2026
Finished Sq Ft:
4,885
Total Sq Ft:
6,062
Lot Size:
17,570 sqft / 0.40 acres (approx)
Year Built:
1990
See this Listing
Schools
Interior
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer, Wine Refrigerator
Bathrooms
5 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Ceramic Tile, Laminate, Hardwood
Heating
Central
Interior Features
Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Walk-In Closet(s)
Laundry Features
Laundry Room
Levels
Two
Exterior
Attached Garage YN
1
Community Features
Buyer Approval Required, Clubhouse, Deed Restrictions, Fitness Center, Gated Community – Guard, Golf Carts OK, Golf, Irrigation-Reclaimed Water, Park, Playground, Pool, Restaurant, Sidewalks, Tennis Court(s)
Construction Materials
Stucco
Covered Spaces
2
Direction Faces
South
Exterior Features
Outdoor Grill, Outdoor Kitchen
Garage Spaces
2
Roof
Tile
Financial
HOA Fee
$2,900
HOA Fee Frequency
Semi-Annually
HOA Includes
24-Hour Guard, Community Pool, Manager, Pool Maintenance, Private Road, Security
HOA Name
Access Management/ Hope Root
HOA Phone
813-607-2220
Tax Year
2025
Taxes
$16,651
Map
Community
- Address97 SUGAR MILL DRIVE OSPREY FL
- SubdivisionOAKS
- CityOSPREY
- CountySarasota
- Zip Code34229
Subdivisions in OSPREY
- ACREAGE & UNREC
- ARBORS
- BAY ACRES – RESUB
- BAY OAKS ESTATES
- BAY OAKS ESTATES UNIT 1
- BAY STREET
- BAY STREET VILLAGE
- BAYPOINTE VISTA 1
- BAYSIDE
- BISHOPS COURT AT OAKS PRESERVE
- BISHOPSCOURT AT THE OAKS PRESERVE
- BISHOPSCOURT TOWNHOME ONE
- BLACKBURN HARBOR RESIDENCES
- BLACKBURN HARBOR WATERFRONT VILLAS
- BLACKBURN HARBOR WATERFRONT VILLAS PHASE 2
- BLACKBURN POINT WOODS
- CASEY KEY
- CORDES COVE
- DRY SLIPS AT BELLAGIO VILLAGE
- EDGEWATER/HIDDEN BAY PH 1 BLDG
- EDGEWATER/HIDDEN BAY PH 3
- EDGEWATER/HIDDEN BAY PH II BLD
- HARMS SUB
- HERON BAY CLUB SEC I
- HERON HOUSE
- HIDDEN BAY
- MERIDIAN AT THE OAKS PRESERVE
- NORTH CREEK ESTATES
- OAKS
- OAKS 2 PH 1
- OAKS 2 PH 2
- OAKS 2 PH 4-C PT 3
- OAKS 2 PHASE 2
- OAKS 3 PH 1
- OSPREY EXECUTIVE PARK
- OSPREY HARBOR CLUB
- OSPREY PARK 2
- PALMS/CASEY KEY
- PARK TRACE ESTATES
- PHASE 1 OF BAY STREET
- PHASE 2 OF BAY STREET
- PINE RANCH
- PINE RANCH EAST
- PINE RUN I
- PINE RUN II
- PINE RUN III
- RIVENDELL
- RIVENDELL THE WOODLANDS
- RIVENDELL WOODLANDS
- SARABAY ACRES
- SAUNDERS V A RESUB
- SIESTA REV RESUB OF PT
- SORRENTO SHORES
- SORRENTO VILLAS 1
- SOUTH CREEK
- SOUTHBAY YACHT & RACQUET CLUB
- THE OAKS
- THE OAKS BAYSIDE
- TOWNS-END SHORES
- VILLAS AT BELLAGIO HARBOR VILLAGE
- VILLAS AT OSPREY HARBOR VILLAGE
- VILLAS AT THE OSPREY HARBOR VILLAGE
- VILLAS/HARBOR VILLAGE
- WILLOWBEND PH 1
- WILLOWBEND PH 3
- WILLOWBEND PH 4
- WILLOWBEND PHASE 3
- WINDSOR LODGE AT THE OAKS
Market Summary
Current real estate data for Single Family in OSPREY as of May 03, 2026
104
Single Family Listed
145
Avg DOM
460
Avg $ / SqFt
$1,414,355
Avg List Price
Property Summary
- Located in the OAKS subdivision, 97 SUGAR MILL DRIVE OSPREY FL is a Single Family for sale in OSPREY, FL, 34229. It is listed for $1,950,000 and features 5 beds, 6 baths, and has approximately 4,885 square feet of living space, and was originally constructed in 1990. The current price per square foot is $399. The average price per square foot for Single Family listings in OSPREY is $460. The average listing price for Single Family in OSPREY is $1,414,355. To schedule a showing of MLS#a4691789 at 97 SUGAR MILL DRIVE in OSPREY, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
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Courtesy of PALM PARADISE REALTY GROUP. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 97 SUGAR MILL DRIVE
OSPREY, FL

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