404 E Macewen Dr, Osprey, FL 34229
Property image
Property image
OFF MARKET

404 E Macewen Dr
Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 3,454 sqft (on 0.62 acres)

$1,335,600

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $8,271/mo*
Refinance Your Home

$1,335,600

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $8,271/mo*
Refinance Your Home
3 Beds
3 Baths
3,454 sqft
(on 0.62 acres)

Local Information

  • Map ViewExplore the area around 404 E Macewen 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
0.62 acres
Living Area
3,454 sqft
Price/Sqft
$387
Parking
Garage

About this House

This architect-designed, custom-built 3 bedroom, 3 bath home will captivate you from the moment you see it. Situated in The Oaks Clubside, as you enter your eyes will be drawn to the incredible lake and golf course views beyond the lanai, expanded and enhanced by the ten foot pocket sliders in the living room and dining room. The spacious 3,400 + square foot interior offers plenty of room to live the country club lifestyle with comfort and ease. As you explore the home you will be delighted by all the special touches you find; beautiful 12 inch baseboards in the study, crown moldings, diagonally laid tile, a charming kitchen with breakfast bar, and dining nook with large aquarium window affording you with gorgeous open views. The lanai is the spot for those who want to enjoy outdoor living; offering large covered areas to dine under or just sit in the shade with a cool drink, a pool and spa. With a southern exposure, you can spend your days enjoying the sunshine, and the brilliant colors of the green grass and blue skies. In the evening enjoy the ripple of the water in the lake, reflecting the sun, as it sets on another perfect Florida day. The Oaks is Sarasota's premier golf and country club. With two championship golf courses, 12 HAR-TRU tennis courts (4 lighted), state-of-the-art fitness center, three outstanding restaurants and a wealth of social events and cultural and recreational activities. This Distinguished Emerald Club offers something for everyone. Membership is available and required.
404 E Macewen Dr, Osprey, FL 34229 is a 3 bedroom, 3 bathroom, 3,454 sqft single-family home built in 2000. It last sold for $925,000 on Mar 26, 2021. It is currently off market. The Trulia Estimate is $1,335,600, with a rent estimate of $6,296/month.

Home Details for 404 E Macewen Dr

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
Number of Rooms: 9Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
DishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa
Hot Tub or Spa
Levels, Entrance, & Accessibility
Floors: Tile, Carpet

Exterior Features

Exterior Home Features
Roof: TileExterior: Other, StuccoFoundation Type: ConcretePatio
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

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

Community

Units in Building: 1

Lot Information

Lot Area: 0.62 acres

Price History for 404 E Macewen Dr

DatePriceEventSource
03/26/2021$925,000Sold
N/A
02/10/2021$925,000PendingAgent Provided
02/10/2021$925,000Listed For SaleAgent Provided
01/20/2020$900,000ListingRemovedAgent Provided
12/12/2019$900,000Listed For SaleAgent Provided
03/29/2018$845,000Sold
N/A
02/04/2018$870,000PendingAgent Provided
02/04/2018$870,000Listed For SaleAgent Provided
02/20/2015$690,000Sold
Stellar MLS #A4106675
01/29/2015$749,000PendingAgent Provided
10/20/2014$749,000Listed For SaleAgent Provided
05/02/2011$560,000Sold
N/A
03/05/2011$590,000PendingAgent Provided
02/24/2011$590,000PriceChange
Agent Provided
02/11/2011$685,000PriceChange
Agent Provided
12/03/2010$765,000PriceChange
Agent Provided
03/21/2010$847,000Listed For SaleAgent Provided
06/07/1999$156,000Sold
N/A
12/30/1998$144,000Sold
N/A
12/31/1996$90,000Sold
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$13,782
Assessment$1,149,500
Home facts updated by county records

Comparable Sales for 404 E Macewen Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
600 EAGLE WATCH LANE, Osprey, FL
0.26
Single-Family Home
$2,035,000
06/18/26
3
3
3,681
434 MACEWEN DRIVE, Osprey, FL
0.33
Single-Family Home
$1,385,000
06/23/26
3
3
2,414
402 WALLS WAY, Osprey, FL
0.34
Single-Family Home
$1,325,000
11/07/25
4
3.5
3,464
264 SARATOGA COURT, Osprey, FL
0.20
Single-Family Home
$2,300,000
11/05/25
4
3.5
3,857
401 WALLS WAY, Osprey, FL
0.32
Single-Family Home
$1,700,000
07/17/26
4
3.5
4,387
113 BURNEY ROAD, Osprey, FL
0.64
Single-Family Home
$965,000
07/31/26
3
2.5
2,502
898 MACEWEN DRIVE, Osprey, FL
0.41
Single-Family Home
$1,700,000
09/18/25
4
4
4,132
228 SAINT JAMES PARK, Osprey, FL
0.38
Single-Family Home
$1,600,000
05/14/26
3
2.5
2,425
462 E MACEWEN DRIVE, Osprey, FL
0.56
Single-Family Home
$1,500,000
09/19/25
3
2.5
2,611
462 E Mac Ewen Dr, Osprey, FL
0.58
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 404 E Macewen 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 404 E Macewen Dr

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Off Market Homes Near 404 E Macewen Dr

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Frequently asked questions about 404 E Macewen Dr

  • What is 404 E Macewen Dr estimated to be worth?
    Trulia's estimated value for 404 E Macewen Dr in Osprey, FL is $1,335,600.
  • What is the price history for 404 E Macewen Dr?
    404 E Macewen Dr in Osprey, FL last sold for $925,000 in March 2021.
  • 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 404 E Macewen Dr have air conditioning?
    Yes, 404 E Macewen Dr in Osprey, FL has air conditioning.
  • Does 404 E Macewen Dr have a pool?
    Yes, 404 E Macewen Dr in Osprey, FL has a pool.