365 Mac Ewen Dr, Osprey, FL 34229
OFF MARKET

365 Mac Ewen Dr
Osprey, FL 34229

  • 4 Beds
  • 5 Baths
  • 5,151 sqft (on 0.62 acres)

$1,615,100

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $9,875/mo*
Refinance Your Home

$1,615,100

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $9,875/mo*
Refinance Your Home
4 Beds
5 Baths
5,151 sqft
(on 0.62 acres)

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

Experience an elegant country club lifestyle on a remarkable interior lot behind the gates of Sarasota's most sought-after community, The Oaks. A lush, tree-shaded paver drive leads to the leaded glass entry doors of this comfortable four-bedroom home, where a spacious, boldly decorated floor plan creates a perfect haven for grand entertaining or relaxed family living. Rich with fine touches throughout its graceful common spaces, including high ceilings, extensive crown molding and wainscoting, French doors, wood floors and marble accents, this sprawling estate exudes a welcoming Southern feeling with striking appeal. With large, open areas for gatherings, the gracious layout boasts a split plan with sizeable bedrooms, a library with built-in shelving, and a wet bar and fireplace in the family and living rooms. Delight in calm afternoons on the expansive screened lanai and pool area backing the meticulously kept Heron Course. Ace-dura flo installed for plumbing. Conveniently located to shopping, I75, fine schools, & America's #1 beach. The Oaks Club amenities include 2 18-hole golf courses, tennis, croquet & fine dining. Oaks Club membership required.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Patio, Pool
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No Info
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 365 Mac Ewen Dr

Interior Features

Heating & Cooling
Heating: CentralAir ConditioningCooling System: CentralHeating Fuel: Central
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet
Interior Details
Number of Rooms: 7
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: OtherExterior: StuccoFoundation Type: ConcretePatio
Pool
Pool
Parking & Garage
GarageParking: Garage, Open

Property Information

Year Built
Year Built: 1989Year Updated: 1999
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.62 acres

Price History for 365 Mac Ewen Dr

DatePriceEventSource
10/13/2013$1,100,000ListingRemovedAgent Provided
02/01/2013$1,100,000Listed For SaleAgent Provided
12/03/2003$155,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$10,923
Assessment$1,350,200
Home facts updated by county records

Comparable Sales for 365 Mac Ewen Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
421 E Mac Ewen Dr, Osprey, FL
0.35
Single-Family Home
$565,000
05/27/25
4
4
3,784
264 Saratoga Ct, Osprey, FL
0.17
Single-Family Home
$2,300,000
11/05/25
4
3.5
3,857
402 Walls Way, Osprey, FL
0.25
Single-Family Home
$1,325,000
11/07/25
4
3.5
3,464
624 Eagle Watch Ln, Osprey, FL
0.42
Single-Family Home
$2,500,000
06/23/25
4
5
5,922
896 Mac Ewen Dr, Osprey, FL
0.44
Single-Family Home
$2,300,000
04/06/26
4
5.5
4,858
898 Mac Ewen Dr, Osprey, FL
0.42
Single-Family Home
$1,700,000
09/18/25
4
4
4,132
223 Saint James Park, Osprey, FL
0.20
Single-Family Home
$1,197,000
05/30/25
3
4
3,321
453 E Macewen Dr, Osprey, FL
0.61
Single-Family Home
$1,850,000
01/22/26
4
3.5
4,191
889 Mac Ewen Dr, Osprey, FL
0.57
Single-Family Home
$2,100,000
01/30/26
4
4
3,235
691 Eagle Watch Ln, Osprey, FL
0.51
Single-Family Home
$3,650,000
04/06/26
4
6
6,705

Nearby homes

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Assigned Schools

These are the assigned schools for 365 Mac Ewen Dr.
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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

  • 53 % Say neighbors are friendly

  • 48 % Say there are sidewalks

  • 42 % Say it's walkable to restaurants

  • 42 % Say streets are well-lit

  • 41 % Say there are community events

  • 40 % Say it's walkable to grocery stores

  • 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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365 Mac Ewen Dr, Osprey, FL 34229 is a 4 bedroom, 5 bathroom, 5,151 sqft single-family home built in 1989. This property is not currently available for sale. 365 Mac Ewen Dr was last sold on Dec 3, 2003 for $155,000. The current Trulia Estimate for 365 Mac Ewen Dr is $1,615,100.