433 E MACEWEN DRIVE, Osprey, FL 34229
Property image
Property image
UNDER CONTRACT
3D VIEW
0.61 ACRES

433 E MACEWEN DRIVE
Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 4,012 sqft (on 0.61 acres)

$2,189,000

Est. Mortgage $13,649/mo*
Get Pre-Qualified

$2,189,000

Est. Mortgage $13,649/mo*
Get Pre-Qualified
4 Beds
3.5 Baths
4,012 sqft
(on 0.61 acres)

Home Highlights

Parking
3 Car Garage
Outdoor
Pool
Climate Control
Heating & Cooling
HOA
$142/Monthly
Price/Sqft
$546
Listed
180+ days ago

Local Information

  • Map ViewExplore the area around 433 E MACEWEN DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Under contract-accepting backup offers. **EXPERIENCE TIMELESS ELEGANCE AND EXCEPTIONAL CRAFTSMANSHIP** in this impeccably maintained Arthur Rutenberg custom residence, perfectly positioned on a private 0.61-acre homesite overlooking the Heron Golf Course with tranquil water views in the prestigious, 24-hour gated Oaks Club community. Nestled beneath a gorgeous oak canopy and enhanced by professional exterior landscape lighting, this remarkable 4,012-square-foot home offers the utmost in Florida living. Designed to maximize natural light, soaring 12-foot ceilings, expansive windows, and seamless indoor-outdoor living, the home was affectionately known by its previous owners as "The House of Light." From the dramatic circular driveway and lighted entrance columns to the elegant coffered ceilings, crown molding, and inviting gas fireplace, every detail reflects the quality and sophistication synonymous with Arthur Rutenberg. The thoughtfully designed floor plan features 4 Bedrooms plus Private Study/Den, 3 Full and 1 Falf Baths, centered around a spacious gourmet kitchen with new granite countertops, premium Sub-Zero and Wolf stainless steel appliances, and an open flow into the comfortable family room—ideal for both everyday living and entertaining. The luxurious primary suite offers a spa-inspired bath with dual vanities, a custom tiled walk-in shower, and a relaxing soaking tub. An oversized three-car garage provides abundant storage, a workbench, and an additional refrigerator. The expansive screened lanai is the true centerpiece of the home, offering the ultimate Florida lifestyle with generous covered entertaining space, multiple dining areas, and a stunning pool highlighted by a dramatic four-foot tiled waterfall feature. A fully equipped outdoor kitchen includes granite countertops, an Alfresco grill, refrigerator, and bar seating, creating the perfect setting for year-round entertaining. Meticulously updated throughout the years, significant improvements include hurricane-impact windows and doors (2020), roof (2019), pool cage/aluminum structure (2018), and numerous additional enhancements that preserve the home's exceptional quality and value. The Oaks Club is a member-owned private golf community with more than 40 years of excellence and is the only private residential golf club in the Sarasota, Bradenton, and Fort Myers region recognized by both Platinum Clubs of America and Distinguished Emerald Clubs of the World. Residents enjoy a magnificent 30,000-square-foot clubhouse, three exceptional dining venues, two championship 18-hole golf courses, outstanding golf instruction, a premier racquet program with 12 Har-Tru HydroGrid tennis courts and pickleball courts, croquet, bocce, basketball, a Junior Olympic swimming pool, and a newly expanded state-of-the-art wellness, fitness, and spa facility. Recognized as "The Healthiest Club" and an Audubon Society-certified community, The Oaks also welcomes families and offers an unmatched lifestyle. Ideally located in one of Sarasota County's most sought-after communities, this exceptional home is just minutes from world-renowned beaches, top-rated schools, fine dining, shopping, and Sarasota's vibrant arts and cultural attractions, making it a rare opportunity to enjoy luxury living in a truly prime location. **Enjoy Viewing the 3D Virtual Tour and Aerial Video*

Home Details for 433 E MACEWEN DRIVE

Interior Features

Interior Details
Number of Rooms: 12Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Primary Bathroom, Balcony Porch Lanai, Dinette, Dining Room, Family Room, Kitchen, Living Room, Studio
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4012 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Public, Sprinkler Well, Street Lights, Underground UtilitiesAppliances: Bar Fridge, Oven, Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range Hood, Refrigerator, Washer, Wine RefrigeratorDishwasherDisposalDryerLaundry: Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,Heat Pump,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Gas, Living RoomSpa: Heated, In GroundHas a FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Window Treatments, Hurricane ShuttersDoor: Outdoor Grill, Outdoor Kitchen, Sliding DoorsFlooring: Carpet, Ceramic Tile, Marble, Slate, Hardwood
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Carpet, Ceramic Tile, Marble, Slate, Hardwood
View
Has a ViewView: Golf Course, Pool, Pond
Security
Security: Gated Community, Security System Owned, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: ScreenedVegetation: Mature Landscaping, Trees/LandscapedOther Structures: Outdoor KitchenExterior: Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Rain GuttersFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Circular Driveway,Driveway,Garage Door Opener,Garage Faces Rear,Garage Faces Side
Pool
Pool: Auto Cleaner, Gunite, Heated, In Ground, Other, Screen Enclosure, Solar HeatPool
Frontage
Road Frontage: Private RoadResponsible for Road Maintenance: Private Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 212Days on Market: 180+

Property Information

Year Built
Year Built: 1998
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Custom,Florida
Building
Construction Materials: Block, StuccoNot a New ConstructionNo Additional ParcelsDoes Not Include Home Warranty
Property Information
Condition: CompletedParcel Number: 0141150001

Price & Status

Price
List Price: $2,189,000Price Per Sqft: $546
Status Change & Dates
Off Market Date: Mon Aug 03 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: Pending

Media

Location

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

Agent Information

Listing Agent
Listing ID: A4676505

Building

Building Area
Building Area: 5670 Square Feet
Community rooms
Fitness Center

Community

Community Features: Clubhouse, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf, Playground, Pool, Restaurant, Tennis Court(s)Not Senior Community
Other
Playground

HOA

HOA Fee Includes: 24-Hour Guard, Common Area Taxes, Reserve Fund, Recreational FacilitiesHOA Name: ACCESS MANAGEMENTHOA Phone: 813-607-2220Association for this Listing: Sarasota - ManateeHas an HOAHOA Fee: $142/Monthly

Lot Information

Lot Area: 0.61 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: A4676505Zillow Contingency Status: Under ContractWater ViewWater View: PondBack On Market Date: Thu Jul 23 2026Showing AttendedShowing Considerations: No SignShowing Requirements: Listing Agent Must Accompany, ShowingTimeUniversal Property Id: US-12115-N-0141150001-R-N

Additional Information

HOA Amenities: Basketball Court,Clubhouse,Fence Restrictions,Fitness Center,Gated,Pickleball Court(s),Playground,Pool,Recreation Facilities,Security,Tennis Court(s),Vehicle Restrictions
Last check for updates: about 17 hours ago
Listing Provided by: Mark Lyda, (941) 586-2670
GENEROUS PROPERTY, (941) 275-9399
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#A4676505
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

Market trends in Osprey

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
139
17MoM

Price History for 433 E MACEWEN DRIVE

DatePriceEventSource
08/04/2026$2,189,000ContingentStellar MLS #A4676505
06/23/2026$2,189,000PriceChange
Stellar MLS #A4676505
01/02/2026$2,250,000PendingToActiveStellar MLS #A4676505
12/31/2025$2,250,000PendingStellar MLS #A4676505
12/30/2025$2,250,000Listed For SaleStellar MLS #A4676505
11/03/2022$2,000,000Sold
N/A
09/22/2022$2,150,000PendingStellar MLS #A4547984
09/22/2022$2,150,000Listed For SaleStellar MLS #A4547984
07/17/2017$1,150,000Sold
N/A
05/03/2017$1,200,000PendingAgent Provided
03/27/2017$1,200,000PendingToActiveAgent Provided
03/26/2017$1,200,000PendingAgent Provided
03/26/2017$1,200,000Listed For SaleAgent Provided
02/24/2011$800,000Sold
N/A
06/27/2010$899,000PriceChange
Agent Provided
06/26/2010$925,000PriceChange
Agent Provided
03/19/2010$995,000PriceChange
Agent Provided
09/26/2009$1,275,000PriceChange
Agent Provided
01/31/2009$1,450,000Listed For SaleAgent Provided
11/23/2008$1,400,000ListingRemovedAgent Provided
11/17/2008$1,400,000Listed For SaleAgent Provided
04/14/2006$1,620,000Sold
Stellar MLS #A287535
07/11/2002$932,500Sold
N/A
03/06/1997$163,500Sold
N/A

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Property Tax and Assessment

Year2025
Tax$17,426
Assessment$1,537,100
Home facts updated by county records

Comparable Sales for 433 E MACEWEN DRIVE

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
453 E MACEWEN DRIVE, Osprey, FL
0.23
Single-Family Home
$1,850,000
01/22/26
4
3.5
4,191
600 EAGLE WATCH LANE, Osprey, FL
0.21
Single-Family Home
$2,035,000
06/18/26
3
3
3,681
898 MACEWEN DRIVE, Osprey, FL
0.33
Single-Family Home
$1,700,000
09/18/25
4
4
4,132
264 SARATOGA COURT, Osprey, FL
0.37
Single-Family Home
$2,300,000
11/05/25
4
3.5
3,857
434 MACEWEN DRIVE, Osprey, FL
0.04
Single-Family Home
$1,385,000
06/23/26
3
3
2,414
401 WALLS WAY, Osprey, FL
0.47
Single-Family Home
$1,700,000
07/17/26
4
3.5
4,387
896 MACEWEN DRIVE, Osprey, FL
0.35
Single-Family Home
$2,300,000
04/06/26
4
5.5
4,858
889 MACEWEN DRIVE, Osprey, FL
0.52
Single-Family Home
$2,100,000
01/30/26
4
4
3,235
402 WALLS WAY, Osprey, FL
0.46
Single-Family Home
$1,325,000
11/07/25
4
3.5
3,464

Nearby homes

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Assigned Schools

These are the assigned schools for 433 E MACEWEN DRIVE.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

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Frequently asked questions about 433 E MACEWEN DRIVE

  • What is the estimated monthly payment for 433 E MACEWEN DRIVE?
    Based on a $2,189,000 list price with 20% down at today's rates, the estimated monthly payment for 433 E MACEWEN DRIVE in Osprey, FL is approximately $13,757 (about $11,365 principal & interest, $2,317 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 433 E MACEWEN DRIVE?
    The closest schools to 433 E 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 433 E MACEWEN DRIVE estimated to be worth?
    Trulia's estimated value for 433 E MACEWEN DRIVE in Osprey, FL is $2,047,700.
  • Does 433 E MACEWEN DRIVE have air conditioning?
    Yes, 433 E MACEWEN DRIVE in Osprey, FL has air conditioning.
  • Does 433 E MACEWEN DRIVE have a pool?
    Yes, 433 E MACEWEN DRIVE in Osprey, FL has a pool.
Mark Lyda, GENEROUS PROPERTY, (941) 275-9399
Agent Phone: (941) 586-2670
433 E MACEWEN DRIVE, Osprey, FL 34229 is a 4 bedroom, 4 bathroom, 4,012 sqft single-family home built in 1998. This property is currently available for sale and was listed by Stellar MLS on Dec 30, 2025. The MLS # for this home is MLS# A4676505.