Virtually Staged. A rare canvas of luxury, positioned on a lush double lot within the highly sought-after, gated community of The Oaks, located in Osprey, adjacent to stunning Sarasota, known for The Arts. Bordering the Heron Course on the 8th Fairway, this iconic two-story estate boasts incredible opportunity for limitless potential. Entire interior is freshly painted, to enhance vision of stateliness. With 5 bedrooms, 7.5 bathrooms, and a sprawling layout, this magnificent property is an exceptional backdrop, just waiting for your personal touch. Arrive in style via the elegant front circular driveway, or utilize the private rear driveway leading to a rare 4-car garage. Inside, the home is masterfully designed for both grand entertaining and everyday comfort, with a sweeping curved stairway at the entrance, setting the stage to an exquisite residence. The first floor features a formal living room and a sun-drenched family room complete with a fireplace, custom built-ins, and multiple French doors, leading to the outdoor bliss. A screened lanai lays the foundation for Florida living at its finest, showcasing an enormous 33×46 sparkling heated pool & spa, expansive patio, and an outdoor kitchen. The expansive open kitchen is a chef’s dream, flowing seamlessly into a casual breakfast nook. For formal affairs, the large dining room offers custom cabinetry and an adjacent wet bar. The main-floor master retreat is a true sanctuary, featuring a dedicated sitting area and luxurious his-and-hers en-suite bathrooms. There is more closet space than a clothes diva could possibly desire. The first floor is completed by a handsome office/library with built-ins, a powder room, and a guest bedroom. Upstairs, you will find three additional en-suite bedrooms, one of which benefits from private back-staircase access—ideal for an au pair, in-laws, or VIP guests. With every bedroom featuring its own private bath, privacy is guaranteed for all. Outdoors, the walled double lot provides a private tropical oasis all with tranquil, serene views. On a practical note: Roof replaced in 2019, with hurricane shutters, for peace of mind. Two 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 calendar of social events, The Oaks is Sarasota’s leading golf and country club.
Property Details
Price:
$1,900,000
MLS #:
A4698153
Status:
Active
Beds:
5
Baths:
7.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
OAKS 2 PH 2
Neighborhood:
34229osprey
Listed Date:
Jul 23, 2026
Finished Sq Ft:
5,986
Total Sq Ft:
7,976
Lot Size:
52,461 sqft / 1.20 acres (approx)
Year Built:
1991
See this Listing
Schools
Elementary School:
Laurel Nokomis Elementary
Middle School:
Laurel Nokomis Middle
High School:
Venice Senior High
Interior
Appliances
Built-In Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
Bathrooms
7 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Zoned
Flooring
Bamboo, Carpet, Marble, Tile, Hardwood
Heating
Central, Electric
Interior Features
Central Vacuum, Chair Rail, Crown Molding, Dry Bar, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Surface Counters, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
Laundry Features
Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
Levels
Two
Exterior
Architectural Style
Custom, Traditional
Association Amenities
Clubhouse, Fitness Center, Gated, Golf Course, Park, Playground, Pool, Tennis Court(s), Vehicle Restrictions, Wheelchair Access
Attached Garage YN
1
Community Features
Buyer Approval Required, Clubhouse, Deed Restrictions, Fitness Center, Gated Community – Guard, Golf, Irrigation-Reclaimed Water, No Truck/RV/Motorcycle Parking, Park, Playground, Pool, Restaurant, Special Community Restrictions, Tennis Court(s), Wheelchair Access
Construction Materials
Block, Stucco
Covered Spaces
4
Direction Faces
North
Exterior Features
Balcony, French Doors, Hurricane Shutters, Irrigation System, Lighting, Outdoor Kitchen, Private Mailbox
Garage Spaces
4
Lot Features
Cleared, Corner Lot, In County, Landscaped, On Golf Course, Oversized Lot
Open Parking YN
1
Parking Features
Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Garage Faces Rear, Garage Faces Side, Oversized, Split Garage
Patio And Porch Features
Covered, Enclosed, Rear Porch, Screened
Roof
Tile
Spa Features
Heated, In Ground
View
Golf Course, Trees/Woods
Window Features
Shutters, Tinted Windows
Financial
HOA Fee
$850
HOA Fee Frequency
Quarterly
HOA Includes
24-Hour Guard, Community Pool, Escrow Reserves Fund, Manager, Private Road, Recreational Facilities
HOA Name
Access Management/ Hope Root
HOA Phone
813-607-2220
Tax Year
2025
Taxes
$11,835
Map
Community
- Address916 MACEWEN DRIVE OSPREY FL
- SubdivisionOAKS 2 PH 2
- CityOSPREY
- CountySarasota
- Zip Code34229
Subdivisions in OSPREY
- ACREAGE & UNREC
- ARBORS
- BAY ACRES – RESUB
- BAY OAKS ESTATES
- BAY OAKS ESTATES UNIT 1
- BAY STREET VILLAGE
- BAY STREET VILLAGES
- BAYPOINTE VISTA 1
- BAYPOINTE VISTA 2
- BAYSIDE
- BISHOPS COURT AT OAKS PRESERVE
- BISHOPS COURT AT THE OAKS PRESERVE
- BISHOPSCOURT AT THE OAKS PRESERVE
- BISHOPSCOURT TOWNHOME ONE
- BLACKBURN HARBOR RESIDENCES
- BLACKBURN HARBOR WATERFRONT VILLAS
- BLACKBURN POINT MARINA VILLAGE
- BLACKBURN POINT WOODS
- CASEY KEY
- CORDES COVE
- DRY SLIPS AT BELLAGIO HARBOR VILLAGE
- DRY SLIPS AT BELLAGIO VILLAGE
- EDGEWATER AT HIDDEN BAY
- EDGEWATER/HIDDEN BAY PH 2 BLDG
- EDGEWATER/HIDDEN BAY PH 3
- EDGEWATER/HIDDEN BAY PH II BLD
- EDGEWATER/HIDDEN BAY PH IL BLD
- EMERALD WOODS AT OAKS 03 PH 02
- HARMS SUB
- HERON BAY CLUB SEC I
- HERON HOUSE
- HIDDEN BAY
- HIDDEN BAY / LAKE VISTA
- MERIDIAN AT THE OAKS
- MERIDIAN AT THE OAKS PRESERVE
- NORTH CREEK ESTATES
- NORTH CREEK ESTS
- OAKS
- OAKS 2 PH 1
- OAKS 2 PH 2
- OAKS 2 PH 4-C PT 3
- OAKS 2 PHASE 2
- OAKS 3 PH 1
- OAKS BAYSIDE
- OGBURNS T B ADD
- OSPREY EXECUTIVE PARK
- OSPREY PARK 2
- PALMER
- 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
- RIVENDELL, THE WOODLANDS AT RIVENDELL
- RIVENDELL, UNIT 3-A
- SARABAY ACRES
- SAUNDERS V A RESUB
- SIESTA REV RESUB OF PT
- SORRENTO EAST
- SORRENTO SHORES
- SORRENTO VILLAS 1
- SOUTH CREEK
- SOUTHBAY YACHT & RACQUET CLUB
- THE OAKS
- THE OAKS BAYSIDE
- TOWNS-END SHORES
- TRINITY ACRES
- VILLAS AT BELLAGIO HARBOR VILLAGE
- VILLAS/HARBOR VILLAGE
- WEBBS W D ADD
- WILLOWBEND PH 1
- WILLOWBEND PH 2
- 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 Jul 24, 2026
83
Single Family Listed
163
Avg DOM
448
Avg $ / SqFt
$1,268,414
Avg List Price
Property Summary
- Located in the OAKS 2 PH 2 subdivision, 916 MACEWEN DRIVE OSPREY FL is a Single Family for sale in OSPREY, FL, 34229. It is listed for $1,900,000 and features 5 beds, 8 baths, and has approximately 5,986 square feet of living space, and was originally constructed in 1991. The current price per square foot is $317. The average price per square foot for Single Family listings in OSPREY is $448. The average listing price for Single Family in OSPREY is $1,268,414. To schedule a showing of MLS#a4698153 at 916 MACEWEN DRIVE in OSPREY, FL, contact your CENTURY 21 Carioti agent at 2392986550.
Similar Listings Nearby
Courtesy of PREMIER SOTHEBY’S INTERNATIONAL REALTY. 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. 916 MACEWEN DRIVE
OSPREY, FL
