440 E Mac Ewen Dr, Osprey, FL 34229
Property image
Property image
OFF MARKET

440 E Mac Ewen Dr
Osprey, FL 34229

  • 3 Beds
  • 4 Baths
  • 3,889 sqft (on 0.55 acres)

$1,754,800

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $10,842/mo*
Refinance Your Home

$1,754,800

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $10,842/mo*
Refinance Your Home
3 Beds
4 Baths
3,889 sqft
(on 0.55 acres)

Local Information

  • Map ViewExplore the area around 440 E Mac Ewen Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1996
Lot Size
0.55 acres
Living Area
3,889 sqft
Price/Sqft
$451
Parking
Garage

About this House

Enjoy elegant Florida living in one of the finest private golf course communities in Southwest Florida. This well maintained and updated custom home sits on the 5th fairway of the "Eagle" course at the Oaks Clubside. The property features lake and golf course views, a new barrel tile roof in 2011, new A/C system in 2009, volume ceilings, and a wonderful outdoor screened in pool area to enjoy a cool dip after a round of golf. Southern exposure provides great sun light both poolside and inside the home. An oversized 3 car garage provides plenty of space for a workshop and plenty of storage space as well. Property is priced competitively as the seller is highly motivated to negotiate a quick sale. Property ownership in The Oaks Club requires a membership to the club. With one of the finest clubhouse facilities of any private club in Southwest Florida, the Oaks Club is a private member owned club and offers 2 18 hole championship golf courses, 12 har-tru tennis courts, croquet lawn, fine dining in 3 different dining areas and a full social calendar for getting together with fellow club members for interesting events.
440 E Mac Ewen Dr, Osprey, FL 34229 is a 3 bedroom, 4 bathroom, 3,889 sqft single-family home built in 1996. It last sold for $625,000 on May 6, 2013. It is currently off market. The Trulia Estimate is $1,754,800, with a rent estimate of $7,082/month.

Home Details for 440 E 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: 8
Fireplace & Spa
Hot Tub or Spa
Security
Security System

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: StuccoFoundation Type: ConcretePatioPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking: Garage, Open

Property Information

Year Built
Year Built: 1996Year Updated: 2001
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.55 acres

Price History for 440 E Mac Ewen Dr

DatePriceEventSource
05/06/2013$625,000Sold
N/A
02/26/2013$669,000PriceChange
Agent Provided
06/14/2012$699,000Listed For SaleAgent Provided
04/12/2011$859,000ListingRemovedAgent Provided
03/12/2011$859,000PriceChange
Agent Provided
10/15/2010$799,000Listed For SaleAgent Provided
02/28/2003$937,500Sold
N/A
04/29/1996$525,000Sold
N/A

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
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Property Tax and Assessment

Year2025
Tax$15,935
Assessment$1,367,900
Home facts updated by county records

Comparable Sales for 440 E Mac Ewen Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
434 MACEWEN DRIVE, Osprey, FL
0.07
Single-Family Home
$1,385,000
06/23/26
3
3
2,414
453 E MACEWEN DRIVE, Osprey, FL
0.25
Single-Family Home
$1,850,000
01/22/26
4
3.5
4,191
453 E Mac Ewen Dr, Osprey, FL
0.25
Single-Family Home
$1,850,000
01/22/26
4
4
4,191
104 PARK TRACE BOULEVARD, Osprey, FL
0.23
Single-Family Home
$545,000
07/10/26
4
3
2,557
600 EAGLE WATCH LANE, Osprey, FL
0.28
Single-Family Home
$2,035,000
06/18/26
3
3
3,681
898 MACEWEN DRIVE, Osprey, FL
0.40
Single-Family Home
$1,700,000
09/18/25
4
4
4,132
462 E MACEWEN DRIVE, Osprey, FL
0.27
Single-Family Home
$1,500,000
09/19/25
3
2.5
2,611
462 E Mac Ewen Dr, Osprey, FL
0.28
Single-Family Home
$1,500,000
09/22/25
3
2.5
2,611
264 SARATOGA COURT, Osprey, FL
0.44
Single-Family Home
$2,300,000
11/05/25
4
3.5
3,857
402 WALLS WAY, Osprey, FL
0.53
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 440 E Mac Ewen Dr.
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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Apartments for Rent

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Homes for sale near 440 E Mac Ewen Dr

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Off Market Homes Near 440 E Mac Ewen Dr

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Frequently asked questions about 440 E Mac Ewen Dr

  • What is 440 E Mac Ewen Dr estimated to be worth?
    Trulia's estimated value for 440 E Mac Ewen Dr in Osprey, FL is $1,754,800.
  • What is the price history for 440 E Mac Ewen Dr?
    440 E Mac Ewen Dr in Osprey, FL last sold for $625,000 in May 2013.
  • Is Osprey a buyer's or seller's market?
    Osprey is currently a buyer's market, based on recent for-sale activity.
  • 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 recently sold homes in Osprey, FL.
  • Does 440 E Mac Ewen Dr have air conditioning?
    Yes, 440 E Mac Ewen Dr in Osprey, FL has air conditioning.
  • Does 440 E Mac Ewen Dr have a pool?
    Yes, 440 E Mac Ewen Dr in Osprey, FL has a pool.