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

423 E Mac Ewen Dr
Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,832 sqft (on 0.70 acres)

$1,505,100

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $9,310/mo*
Refinance Your Home

$1,505,100

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $9,310/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,832 sqft
(on 0.70 acres)

Local Information

  • Map ViewExplore the area around 423 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
2000
Lot Size
0.7 acres
Living Area
3,832 sqft
Price/Sqft
$393
Parking
Garage

About this House

Don't wait to take advantage of this incredible opportunity to live the luxury country club lifestyle on the gorgeous Gulf Coast! Set back on a beautiful corner cul-de-sac lot in The Oaks Clubside, this custom built 4 bedroom. 3.5 bath Rutenberg home offers you everything you would want for your Florida golf lifestyle. The circular drive, and house itself, are framed by large oak trees creating a peaceful park-like setting. Upon entering, you are instantly aware of the abundant quality and the care given to this warm, inviting home. Custom built-ins, crown molding, granite kitchen, and real wood plantation shutters are just the beginning of the features you will find. Add to these a young roof (2013), whole house audio system, a 6 zone A/C system, custom lighting and top-of-the-line appliances and you might think you would never go outside...until you look out over the incredible pool area with golf course views of the 3rd green of The Oaks Heron course. With neutral custom paint colors in the majority of the rooms, and wood and tile floors, this home is literally ready for you to move in, and begin living the life you've always imagined! Minutes to area beaches and just 12 miles south of vibrant downtown Sarasota, The Oaks Club has 2 championship golf courses, 12 HarTru tennis courts (4 lighted) maintained to tournament standards, manicured croquet lawn and Bocce courts, WellFit, a state-of-the-art fitness center, three onsite restaurants offering a variety of year-round fine dining options, and a celebrated social calendar. Club membership is available and required.
423 E Mac Ewen Dr, Osprey, FL 34229 is a 4 bedroom, 4 bathroom, 3,832 sqft single-family home built in 2000. It last sold for $815,000 on Nov 25, 2020. It is currently off market. The Trulia Estimate is $1,505,100, with a rent estimate of $5,601/month.

Home Details for 423 E Mac Ewen Dr

Interior Features

Heating & Cooling
Heating: Forced Air, Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, CarpetGated Entry
Interior Details
AtticNumber of Rooms: 9Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Office, PantryWet Bar
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: TileExterior: StuccoFoundation Type: ConcretePatioSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 2000Year Updated: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.70 acres

Building

Community rooms
Fitness Center
Fitness & Sports
Tennis Court

Price History for 423 E Mac Ewen Dr

DatePriceEventSource
11/25/2020$815,000Sold
N/A
09/24/2020$850,000PendingAgent Provided
08/30/2020$850,000PriceChange
Agent Provided
09/16/2019$900,000PriceChange
Agent Provided
03/18/2019$899,000Listed For SaleAgent Provided
04/18/2017$795,000Sold
N/A
02/28/2017$850,000PendingAgent Provided
01/24/2017$850,000Listed For SaleAgent Provided
12/01/2016$849,900ListingRemovedAgent Provided
05/09/2015$849,900Listed For SaleAgent Provided
03/30/2010$997,000ListingRemovedAgent Provided
04/06/2009$997,000PriceChange
Agent Provided
02/15/2009$1,092,000Listed For SaleAgent Provided
03/02/1999$165,000Sold
N/A
06/16/1998$162,900Sold
N/A
06/08/1995$625,000Sold
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$9,681
Assessment$1,236,500
Home facts updated by county records

Comparable Sales for 423 E Mac Ewen Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
600 EAGLE WATCH LANE, Osprey, FL
0.13
Single-Family Home
$2,035,000
06/18/26
3
3
3,681
898 MACEWEN DRIVE, Osprey, FL
0.30
Single-Family Home
$1,700,000
09/18/25
4
4
4,132
402 WALLS WAY, Osprey, FL
0.36
Single-Family Home
$1,325,000
11/07/25
4
3.5
3,464
434 MACEWEN DRIVE, Osprey, FL
0.13
Single-Family Home
$1,385,000
06/23/26
3
3
2,414
264 SARATOGA COURT, Osprey, FL
0.25
Single-Family Home
$2,300,000
11/05/25
4
3.5
3,857
453 E Mac Ewen Dr, Osprey, FL
0.30
Single-Family Home
$1,850,000
01/22/26
4
4
4,191
453 E MACEWEN DRIVE, Osprey, FL
0.31
Single-Family Home
$1,850,000
01/22/26
4
3.5
4,191
401 WALLS WAY, Osprey, FL
0.37
Single-Family Home
$1,700,000
07/17/26
4
3.5
4,387
462 E MACEWEN DRIVE, Osprey, FL
0.35
Single-Family Home
$1,500,000
09/19/25
3
2.5
2,611
462 E Mac Ewen Dr, Osprey, FL
0.36
Single-Family Home
$1,500,000
09/22/25
3
2.5
2,611

Nearby homes

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Assigned Schools

These are the assigned schools for 423 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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Explore by feature - Pet Friendly

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Homes for sale near 423 E Mac Ewen Dr

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Off Market Homes Near 423 E Mac Ewen Dr

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Frequently asked questions about 423 E Mac Ewen Dr

  • What is 423 E Mac Ewen Dr estimated to be worth?
    Trulia's estimated value for 423 E Mac Ewen Dr in Osprey, FL is $1,505,100.
  • What is the price history for 423 E Mac Ewen Dr?
    423 E Mac Ewen Dr in Osprey, FL last sold for $815,000 in November 2020.
  • 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 423 E Mac Ewen Dr have air conditioning?
    Yes, 423 E Mac Ewen Dr in Osprey, FL has air conditioning.
  • Does 423 E Mac Ewen Dr have a pool?
    Yes, 423 E Mac Ewen Dr in Osprey, FL has a pool.