916 MACEWEN DRIVE, Osprey, FL 34229
Property image
Property image
FOR SALE
3D VIEW
1.2 ACRES

$1,900,000

  • 5 Beds
  • 7.5 Baths
  • 5,986 sqft (on 1.20 acres)

916 MACEWEN DRIVE, Osprey, FL 34229

Est. Mortgage $11,976/mo*
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Home Highlights

Parking
4 Car Garage
Outdoor
Porch, Pool
HOA
$283/Monthly
Price/Sqft
$317
Climate Control
Central, Electric & Central Air, Zoned
Listed
34 days ago

Local Information

  • Map ViewExplore the area around 916 MACEWEN DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Virtually Staged. A rare canvas of luxury, positioned on a lush double lot within the sought-after, gated community of The Oaks, in Osprey, adjacent to stunning Sarasota, known for the arts. Bordering the Heron Course on the eighth fairway, this iconic two-story estate boasts incredible opportunity for limitless potential. The entire interior is freshly painted, to enhance vision of stateliness. With five bedrooms, 7.5 baths 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 four-car garage. Inside, the home is masterfully designed for 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-by-46-foot sparkling heated pool and 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 primary retreat is a sanctuary, featuring a dedicated sitting area and luxurious dual en-suite baths. 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 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 was replaced in 2019, with hurricane shutters, for peace of mind. Two 18-hole championship golf courses, 12 Har-Tru tennis courts (four lighted), croquet and pickleball 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.
Last check for updates: about 4 hours ago
Listing Provided by: Todd Currey, (941) 402-6000
PREMIER SOTHEBY'S INTERNATIONAL REALTY, (941) 364-4000
Amber Davis, (941) 786-4820
PREMIER SOTHEBY'S INTERNATIONAL REALTY, (941) 364-4000
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#A4698153
Also Listed on Stellar MLS.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 916 MACEWEN DRIVE

Interior Features

Interior Details
Number of Rooms: 15Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Primary Bathroom, Balcony Porch Lanai, Bonus Room, Den, Dinette, Dining Room, Family Room, Foyer, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 8Number of Bathrooms (full): 7Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 5986 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Public, Sewer Connected, Sprinkler Recycled, Underground Utilities, Water ConnectedAppliances: Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, WasherDishwasherDisposalDryerLaundry: Electric Dryer Hookup,Inside,Laundry Room,Washer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Wood BurningSpa: Heated, In GroundHas a FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Hurricane Shutters, Hurricane Shutters/WindowsDoor: French Doors, Outdoor KitchenFlooring: Bamboo, Carpet, Marble, Tile, Hardwood
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Bamboo, Carpet, Marble, Tile, Hardwood
View
Has a ViewView: Golf Course, Trees/Woods

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Covered, Enclosed, Rear Porch, ScreenedVegetation: Mature Landscaping, Oak Trees, Trees/LandscapedExterior: Balcony, Irrigation System, Lighting, Outdoor Kitchen, Private MailboxFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 4Number of Covered Spaces: 4No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 4Parking: Circular Driveway,Driveway,Electric Vehicle Charging Station(s),Garage Door Opener,Garage Faces Rear,Garage Faces Side,Oversized,Split Garage
Pool
Pool: Auto Cleaner, Gunite, Heated, In Ground, Lighting, Outside Bath Access, Screen EnclosurePool
Frontage
Road Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 5Days on Market: 34

Property Information

Year Built
Year Built: 1991
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Custom,Traditional
Building
Construction Materials: Block, StuccoNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 0141040016

Price & Status

Price
List Price: $1,900,000Price Per Sqft: $317

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: OSPREYCommunity: OAKS 2 PH 2
School Information
Elementary School: Laurel Nokomis ElementaryJr High / Middle School: Laurel Nokomis MiddleHigh School: Venice Senior High

Agent Information

Listing Agent
Listing ID: A4698153

Building

Building Area
Building Area: 7976 Square Feet
Community rooms
Fitness Center

Community

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 AccessNot Senior Community
Other
Playground

HOA

HOA Fee Includes: 24-Hour Guard, Community Pool, Reserve Fund, Manager, Private Road, Recreational FacilitiesHOA Name: Access Management/ Hope RootHOA Phone: 813-607-2220Association for this Listing: Sarasota - ManateeHas an HOAHOA Fee: $283/Monthly

Lot Information

Lot Area: 1.2043 Acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: A4698153Showing AttendedShowing Requirements: Appointment Only, Key/Agent, Listing Agent Must Accompany, See Remarks, ShowingTimeUniversal Property Id: US-12115-N-0141040016-R-N

Additional Information

HOA Amenities: Clubhouse,Fitness Center,Gated,Golf Course,Park,Playground,Pool,Tennis Court(s),Vehicle Restrictions,Wheelchair Access

Around this home

What Locals Say about Osprey

At least 46 Trulia users voted on each feature.

  • 90 % Say car is needed

  • 87 % Say it's dog friendly

  • 85 % Say it's quiet

  • 84 % Say parking is easy

  • 75 % Say people would walk alone at night

  • 74 % Say there's wildlife

  • 67 % Say yards are well-kept

  • 67 % Say there's holiday spirit

  • 64 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 48 % Say there are sidewalks

  • 42 % Say it's walkable to restaurants

  • 42 % Say streets are well-lit

  • 41 % Say it's walkable to grocery stores

  • 41 % Say there are community events

  • 31 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.
  • Lindsey W.
    "It’s a quiet and low key suburb area of Sarasota county. It’s very accessible to I-75 and Nokomis beach and about a 25 minute drive to siesta key beach. "
    4
    Flag
  • Mary V.
    "I am retired now but my commute to Stickney Point was only about 10 min and downtown was about 25 min during rush hour when there is no construction "
    0
    Flag
  • Mary V.
    "Pineview School is very close, nice safe area for children. CVS and Publix are also close, as well as Historic Spanish Pointe. The beach is ten minutes or less."
    3
    Flag
  • Bob T.
    "I don’t commute....retired. There are no sidewalks here and our street has a large amount of speeders making walking dangerous. Some neighbors park on the county right of way destroying our water flow/drainage which has caused flooding here. Many homes are unkept even though there is an active hoa."
    14
    Flag
  • Bob T.
    "Neighborhood is pet friendly. Wide road we walking dogs. Only problem noticed now is daily construction vehicles speeding in neighborhood."
    1
    Flag
  • Larysathor
    "Well, the Mother Nature taking its tall, water level raised over last ten years and a lot of beaches are washed out to nonexistence."
    0
    Flag
  • Brenda F. D.
    "Neighborhood is beautiful love the area close to everything and beaches and shopping . Local restaurant "
    1
    Flag
  • Michelle C.
    "I've lived in this neighborhood for twenty years +. My neighbors are the friendliest. We all look out for each other and lend a hand when needed. Can't think of anywhere else I'd want to live."
    0
    Flag
  • nancybuscher
    "This quiet, beautifully landscaped, pet friendly subdivision is close to beaches, shopping, restaurants, cultural events in Sarasota and Venice, beside Oscar Scherer State Park for hickers & boaters, and has easy access to airports by way of US41 & I-75."
    0
    Flag
  • info
    "Centrally located, minutes to beaches and shopping"
    1
    Flag
  • bookwoman39
    "Wonderful community, close to Sarasota and all restaurants, cultural activities, etc. The condo development is a designated bird sanctuary. Nice pools, exercise room, community room. Good neighbors. What the development lacks is diversity. "
    0
    Flag
  • trishmainey1111
    "Osprey Florida is one of the most beautiful, accessible communities in Florida. Ten minutes to the white sands beach and ten minutes to I-75. "
    1
    Flag
  • Gail L.
    "I work here, belong to the club and have lived in the neighborhood for the last 12 years it is one of 5 golf communities I have belonged to and bar none my favorite due to the people that live here. They are multicultural, down to earth and just fabulous. This is a community that rates above the rest . it is very common for folks to move up and down in house sizes and styles as their lifestyles change. Give me a call as I'd love to show you around. "
    0
    Flag

Market trends in Osprey

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
133
7MoM

Home Value

Trulia Estimate
$1.79M
Since last month
Decreased$56K (-3%)
Since last year
Increased$235K (+15.2%)
Since last sale
Increased$188K (+11.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +27% in the last 10 years
MonthEstimated value
2026
August 2026$1.79M
July 2026$1.84M
June 2026$1.52M
May 2026$1.51M
March 2026$1.51M
February 2026$1.52M
January 2026$1.51M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
401 WALLS WAY, Osprey, FL
0.06
Single-Family Home
$1,700,000
07/17/26
4
3.5
4,387
402 WALLS WAY, Osprey, FL
0.05
Single-Family Home
$1,325,000
11/07/25
4
3.5
3,464
896 MACEWEN DRIVE, Osprey, FL
0.21
Single-Family Home
$2,300,000
04/06/26
4
5.5
4,858
895 MACEWEN DRIVE, Osprey, FL
0.26
Single-Family Home
$2,000,000
02/09/26
3
3.5
4,828
898 MACEWEN DRIVE, Osprey, FL
0.19
Single-Family Home
$1,700,000
09/18/25
4
4
4,132
691 EAGLE WATCH LANE, Osprey, FL
0.29
Single-Family Home
$3,650,000
04/06/26
4
6
6,705
264 SARATOGA COURT, Osprey, FL
0.10
Single-Family Home
$2,300,000
11/05/25
4
3.5
3,857
478 ORISKANY COURT, Osprey, FL
0.38
Single-Family Home
$2,625,000
09/16/25
4
6
5,778
600 EAGLE WATCH LANE, Osprey, FL
0.20
Single-Family Home
$2,035,000
06/18/26
3
3
3,681
889 MACEWEN DRIVE, Osprey, FL
0.33
Single-Family Home
$2,100,000
01/30/26
4
4
3,235

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
922 MACEWEN DRIVE, Osprey, FL 34229
0.04
$2,567,800
5
5
4,443
Off Market
402 WALLS WAY, Osprey, FL 34229
0.05
$1,325,000
4
3.5
3,464
Recently Sold
401 WALLS WAY, Osprey, FL 34229
0.06
$1,700,000
4
3.5
4,387
Recently Sold
406 WALLS WAY, Osprey, FL 34229
0.08
$2,401,900
4
3.5
4,284
Off Market
264 SARATOGA COURT, Osprey, FL 34229
0.10
$2,300,000
4
3.5
3,857
Recently Sold
909 MACEWEN DRIVE, Osprey, FL 34229
0.11
$1,595,000
3
3.5
4,241
For Sale
935 BLUE HERON OVERLOOK, Osprey, FL 34229
0.16
$1,706,500
4
3
3,665
Off Market
588 EAGLE WATCH LANE, Osprey, FL 34229
0.19
$1,902,300
4
4.5
4,686
Off Market
898 MACEWEN DRIVE, Osprey, FL 34229
0.19
$1,842,100
4
4
4,132
Off Market
600 EAGLE WATCH LANE, Osprey, FL 34229
0.20
$2,035,000
3
3
3,681
Recently Sold
896 MACEWEN DRIVE, Osprey, FL 34229
0.21
$2,300,000
4
5.5
4,858
Recently Sold

Price and Tax history

DateEventPrice
Jul 24, 2026
Source: Stellar MLS #A4698153
Listed For Sale
$1,900,000
May 1, 2025
Source: Stellar MLS #A4645012
Sold
$1,600,000
Mar 25, 2025
Source: Stellar MLS #A4645012
Pending
$1,800,000
Mar 24, 2025
Source: Stellar MLS #A4645012
Listed For Sale
$1,800,000
Jun 30, 2005
Source: N/A
Sold
$1,475,000

LGBTQ Local Legal Protections

Todd Currey, PREMIER SOTHEBY'S INTERNATIONAL REALTY, (941) 364-4000
Agent Phone: (941) 402-6000

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Frequently asked questions about 916 MACEWEN DRIVE

  • What is the estimated monthly payment for 916 MACEWEN DRIVE?
    Based on a $1,900,000 list price with 20% down at today's rates, the estimated monthly payment for 916 MACEWEN DRIVE in Osprey, FL is approximately $11,919 (about $9,833 principal & interest, $2,011 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Osprey?
    Residents describe Osprey, FL as dog-friendly, quiet, and easy to park in. Most residents say you need a car. See homes for sale in Osprey, FL.
  • What are the closest schools to 916 MACEWEN DRIVE?
    The closest schools to 916 MACEWEN DRIVE in Osprey, FL are Laurel Nokomis School (Pre-K/Elementary/Middle, rated 8/10), Venice Senior High School (rated 7/10).
  • What is 916 MACEWEN DRIVE estimated to be worth?
    Trulia's estimated value for 916 MACEWEN DRIVE in Osprey, FL is $1,788,700.
  • Does 916 MACEWEN DRIVE have air conditioning?
    Yes, 916 MACEWEN DRIVE in Osprey, FL has air conditioning.
  • Does 916 MACEWEN DRIVE have a pool?
    Yes, 916 MACEWEN DRIVE in Osprey, FL has a pool.
916 MACEWEN DRIVE, Osprey, FL 34229 is a 5 bedroom, 8 bathroom, 5,986 sqft single-family home built in 1991. This property is currently available for sale and was listed by Stellar MLS on Jul 24, 2026. The MLS # for this home is MLS# A4698153.