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

416 E Macewen Dr
Osprey, FL 34229

  • 3 Beds
  • 4 Baths
  • 4,262 sqft (on 0.58 acres)

$1,751,500

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $10,841/mo*
Refinance Your Home

$1,751,500

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $10,841/mo*
Refinance Your Home
3 Beds
4 Baths
4,262 sqft
(on 0.58 acres)

Local Information

  • Map ViewExplore the area around 416 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
2001
Lot Size
0.58 acres
Living Area
4,262 sqft
Price/Sqft
$411
Parking
Garage

About this House

Overlooking a lake with Southern rear exposure and featuring a vista of the entire par 3 Eagle number 5 sits this incredible one owner custom built Oaks home. Built by Tivioli homes and incredibly maintained, this 3 bedroom + office estate home has many wonderful features which includes Cherry wood floors, tray ceilings, crown molding, custom wood and granite kitchen, and a double sided bar for the living room and family room. This home lives great because it is on a cul d' sac, all on one floor and no steps to be found. The exterior features a huge lanai with large covered areas , pool and outdoor kitchen. The pool area is surrounded by disappearing sliding glass doors providing incredible lake and golf course views. Membership in Sarasota's Finest Country Club, The Oaks is available and required. Go to the Oaks Club web site for information. Mandatory Equity or Social Membership into the Club.
416 E Macewen Dr, Osprey, FL 34229 is a 3 bedroom, 4 bathroom, 4,262 sqft single-family home built in 2001. It last sold for $1,500,000 on Nov 30, 2021. It is currently off market. The Trulia Estimate is $1,751,500, with a rent estimate of $5,432/month.

Home Details for 416 E Macewen Dr

Interior Features

Heating & Cooling
Heating: CentralAir ConditioningCooling System: CentralHeating Fuel: Central
Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet
Interior Details
Number of Rooms: 8
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: 2001Year Updated: 2006
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.58 acres

Price History for 416 E Macewen Dr

DatePriceEventSource
12/01/2024$1,595,000ListingRemovedStellar MLS #A4512910
12/01/2023ListingRemovedStellar MLS #A4512910
11/30/2021$1,500,000Sold
N/A
10/15/2021$1,595,000PendingStellar MLS #A4512910
10/11/2021$1,595,000PriceChange
Stellar MLS #A4512910
09/29/2021$1,775,000Listed For SaleStellar MLS #A4512910
02/07/2014$890,000Sold
N/A
12/11/2013$989,000Listed For SaleAgent Provided
03/16/2000$160,000Sold
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
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$16,346
Assessment$1,369,100
Home facts updated by county records

Comparable Sales for 416 E Macewen Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
434 MACEWEN DRIVE, Osprey, FL
0.18
Single-Family Home
$1,385,000
06/23/26
3
3
2,414
600 EAGLE WATCH LANE, Osprey, FL
0.21
Single-Family Home
$2,035,000
06/18/26
3
3
3,681
264 SARATOGA COURT, Osprey, FL
0.27
Single-Family Home
$2,300,000
11/05/25
4
3.5
3,857
401 WALLS WAY, Osprey, FL
0.39
Single-Family Home
$1,700,000
07/17/26
4
3.5
4,387
898 MACEWEN DRIVE, Osprey, FL
0.38
Single-Family Home
$1,700,000
09/18/25
4
4
4,132
453 E MACEWEN DRIVE, Osprey, FL
0.41
Single-Family Home
$1,850,000
01/22/26
4
3.5
4,191
402 WALLS WAY, Osprey, FL
0.40
Single-Family Home
$1,325,000
11/07/25
4
3.5
3,464
453 E Mac Ewen Dr, Osprey, FL
0.41
Single-Family Home
$1,850,000
01/22/26
4
4
4,191
896 MACEWEN DRIVE, Osprey, FL
0.40
Single-Family Home
$2,300,000
04/06/26
4
5.5
4,858
462 E MACEWEN DRIVE, Osprey, FL
0.45
Single-Family Home
$1,500,000
09/19/25
3
2.5
2,611

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 416 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

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

13 pet-friendly rentals in Osprey, FL

Explore by feature - Garage

11 rentals with a garage in Osprey, FL

Explore by feature - Air Conditioning

20 rentals with air conditioning in Osprey, FL

Explore by feature - Pool

27 rentals with a pool in Osprey, FL

Explore by feature - Washer/dryer

20 rentals with a washer/dryer in Osprey, FL

Homes for sale near 416 E Macewen Dr

Skip to last item
Skip to first item

Off Market Homes Near 416 E Macewen Dr

Skip to last item
Skip to first item

Frequently asked questions about 416 E Macewen Dr

  • What is 416 E Macewen Dr estimated to be worth?
    Trulia's estimated value for 416 E Macewen Dr in Osprey, FL is $1,751,500.
  • What is the price history for 416 E Macewen Dr?
    416 E Macewen Dr in Osprey, FL last sold for $1,500,000 in November 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 416 E Macewen Dr have air conditioning?
    Yes, 416 E Macewen Dr in Osprey, FL has air conditioning.
  • Does 416 E Macewen Dr have a pool?
    Yes, 416 E Macewen Dr in Osprey, FL has a pool.