5417 Osprey Isle Ln

Windermere, FL 34786

$4,899,000
Price
6
Beds
8,267 Sq. Ft.
$593 / Sq. Ft.
8,267
Sq. Ft.
$593
per Sq. Ft.
Pending
Pending
an aerial view of a house with outdoor space and lake view
a front view of a house with a garden
a front view of a house with a yard
a living room with furniture and a large mirror
a living room with fireplace furniture and a chandelier
a living room with a couch and a fireplace
a large kitchen with a table and chairs
a living room with furniture and a fireplace
a living room with furniture and a flat screen tv
a kitchen with stainless steel appliances kitchen island granite countertop a stove and a sink with cabinets
a kitchen with kitchen island granite countertop wooden cabinets and stainless steel appliances
a kitchen with kitchen island granite countertop wooden cabinets and a granite counter tops
a kitchen with stainless steel appliances granite countertop a stove and a sink
a bathroom with a sink toilet and shower
a view of an empty room with large windows and a table
a bathroom with a sink a toilet and tub
a kitchen with stainless steel appliances kitchen island granite countertop a stove top oven a sink and cabinets
a kitchen with granite countertop a stove a refrigerator and a dining table
a view of a dining room with furniture window and outside view
a kitchen with stainless steel appliances granite countertop a refrigerator and a sink
a living room with furniture and a mirror
a bedroom with a bed and glass windows
a bedroom with a large bed and a chandelier
a bedroom with a bed and glass windows
a view of sky from balcony
a view of kitchen with granite countertop cabinets and refrigerator
a living room with furniture and a flat screen tv
a spacious bathroom with a tub sink a mirror and a shower
a bathroom with a tub sink and mirror
a kitchen with stainless steel appliances granite countertop a stove and a sink
a room with lots of furniture and wooden floor
a room with wooden floor pool table and windows
a view of room with window
a view of a house with barbeque grill and couches
a view of balcony
a view of balcony with city view
a view of kitchen with kitchen island and living room
a view of a lake with couches
a view of a balcony with chairs
a outdoor living space with furniture
an aerial view of a house
a view of a lake in middle of the town

Description

Dr. Phillips Isle of Osprey. Custom lakefront home with beautiful panoramic views of Lake Blanche. The moment you enter, you are welcomed by the 2-story view of the rock accent pool with waterfall and sparkling lake! This home features 6 ensuite bedrooms (primary and two on the first floor and 3 on the second floor). The grand 2-story stone staircase gently ascends to an iron balcony overlooking the living room under a beamed rotunda ceiling! The kitchen and family room are open and also feature...Dr. Phillips Isle of Osprey. Custom lakefront home with beautiful panoramic views of Lake Blanche. The moment you enter, you are welcomed by the 2-story view of the rock accent pool with waterfall and sparkling lake! This home features 6 ensuite bedrooms (primary and two on the first floor and 3 on the second floor). The grand 2-story stone staircase gently ascends to an iron balcony overlooking the living room under a beamed rotunda ceiling! The kitchen and family room are open and also feature a wet bar, walk in pantry, commercial grade appliances, fireplace and corner sliding doors that open up to the spacious lanai with summer kitchen. Near the primary suite is a spacious office and exercise room, both with separate entrances from the front patio. The primary bath is spacious with dual vanities and a round tub encompassing a lake view. There is also two spacious closets with built in cabinetry. The second floor boasts 3 spacious ensuite bedrooms and a Homework station. There is also a game room with bar and kitchen, media area and theatre that seats six that has corner sliding doors opening up to the balcony with stunning lake views. Travertine and hardwood flooring throughout, architecturally detailed ceilings, stately columns on nearly one acre, this home also has 5 full garages, a new tile roof in 2021, and much more. Located near expressways, shopping and "restaurant row".

Property Details for 5417 Osprey Isle Lane

Architectural Style
Mediterranean
Subdivision Name
ISLE OF OSPREY
Township
23
Garage Spaces
5
View
Water
Waterfront
Yes
Water View
Lake - Chain of Lakes
LISTING UPDATED: 11/20/2025 11:18 AM

Property Details for 5417 Osprey Isle Lane

StatusPending
MLS #O6358658
Days on Market9
Taxes$62,168 / year
HOA Fees$3,500 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built2007
Lot Size0.91 AC / 39,847 SF
CountyOrange County

Location

Listing Courtesy of SOUTHERN REALTY GROUP LLC, Teresa Stewart; SOUTHERN REALTY GROUP LLC, Michael Stewart
Add your commute

Building Information for 5417 Osprey Isle Lane

Stories-Year Built2007Building Size-Lot Size0.91 AC / 39,847 SF

Payment Calculator

$29,680 per month

30 year fixed, 6.28% Interest

Principal and Interest

$24,208

Property Taxes

$5,181

HOA Dues

$292

The Payment Calculator is for illustrative purposes only.

Property Information for 5417 Osprey Isle Lane

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 11589.0
  • Building Area Units: Square Feet
  • Community Features: Water Access, Waterfront, Deed Restrictions, Gated Community - Guard, Golf Carts OK
  • Direction Faces: Southwest
  • Directions: From I-4, West on Conroy, Left on Apopka Vineland, Right on Tarawood, Right on Brookline Drive, Left on Masters Blvd, Right on Osprey Isle, MUST HAVE PRIOR GATE CLEARANCE!
  • Elementary School: Palm Lake Elem
  • Middle Or Junior School: Chain of Lakes Middle
  • High School: Dr. Phillips High
  • Mls Major Change Type: Pending
  • Major Change Type: Pending
  • Listing Service: Full Service
  • Senior Community: No
  • Unit Number: No
  • Street Number: 5417
  • Street Name: OSPREY ISLE
  • State: FL
  • City: ORLANDO
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Driveway, Garage Door Opener, Garage Faces Side, Split Garage
Taxes and HOA Information
  • Association Approval Required: No
  • Association Fee Includes: Security
  • Association Fee Requirement: Required
  • Association Name: Real Manage
  • Association Phone: 866-473-2573
  • Association: Yes
  • CDD: No
  • Pet Restrictions: Refer to HOA docs
  • Tax Block: 000
  • Tax Book Number: 0024/0004
  • Tax Legal Description: ISLE OF OSPREY AT DR PHILLIPS 24/4 LOT 9
  • Tax Lot: 9
  • Tax Year: 2025
Property
Lot Information
  • Additional Parcels: No
  • Lot Features: Cul-De-Sac
  • Parcel Number: 212328387000090
  • Total Acreage: 1/2 to less than 1
  • Water Access: Lake - Chain of Lakes
  • Water Access: Yes
  • Water Body Name: LAKE BLANCHE/BUTLER CHAIN
  • Water Extras: Skiing Allowed
  • Water Extras: Yes
  • Water: Skiing Allowed
  • Zoning: R-1AA
  • Living Area: 8267
Property and Assessments
  • Year Built Numeric: 2007
  • Association Amenities: Security
  • Flood Zone Code: AE
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 28
  • Public Survey Section: 21
  • Dock YN: Yes
  • Dock Description: Dock w/Electric
  • Dock Dimensions: 22x22
Utilities
  • Sewer: Public Sewer
  • Utilities: BB/HS Internet Available, Electricity Connected, Public, Street Lights, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block, Stucco
  • Exterior Features: Balcony, Irrigation System, Outdoor Kitchen, Private Mailbox, Rain Gutters, Sliding Doors
  • Foundation Details: Slab
  • Levels: Two
  • Patio And Porch Features: Covered, Patio
  • Pool Features: Gunite, In Ground
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Tile
  • Security Features: Gated Community, Security System, Smoke Detector(s)
  • Spa: No
  • Vegetation: Mature Landscaping
  • Waterfront Features: Waterfront, Lake - Chain of Lakes
  • Waterfront Feet Total: 162
Interior Features
  • Bedrooms Total: 6
  • Bathrooms Full: 6
  • Additional Rooms: Den/Library/Office, Family Room, Formal Dining Room Separate, Formal Living Room Separate, Inside Utility, Media Room
  • Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Washer
  • Cooling: Central Air
  • Fireplace Features: Family Room, Living Room
  • Fireplace: Yes
  • Flooring: Carpet, Tile, Travertine, Hardwood
  • Heating: Central
  • Interior Features: Built-in Features, Central Vacuum, Coffered Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Smart Home, Solid Wood Cabinets, Split Bedroom, Stone Counters, Tray Ceiling(s), Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments
  • Laundry Features: Inside, Laundry Room
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 12.0
  • Water View: Yes
  • Bathrooms Half: 3
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 5417 Osprey Isle Lane

DateEvent & SourcePriceAppreciation
Nov 19, 2025

Pending

MFRMLS #O6358658

—
Nov 10, 2025

Listed (Active)

MFRMLS #O6358658

$4,899,000—
Aug 3, 2009

Sold (Public Record)

Public Record #273975527

$3,890,000

+32.3% / yr

Aug 3, 2009

Sold

MFRMLS #O4909637

$3,890,000—
Jul 12, 2009

Pending

MFRMLS #O4909637

—
Apr 23, 2009

Listed (Active)

MFRMLS #O4909637

$4,290,000—
Sep 2, 2003

Sold (Public Record)

Public Record #120231079

$742,500—
DateEvent & SourcePrice
11/19/2025

Pending

MFRMLS #O6358658

—
11/10/2025

Listed (Active)

MFRMLS #O6358658

$4,899,000
08/03/2009

Sold (Public Record)

Public Record #273975527

$3,890,000

+32.3% / yr

08/03/2009

Sold

MFRMLS #O4909637

$3,890,000
07/12/2009

Pending

MFRMLS #O4909637

—
04/23/2009

Listed (Active)

MFRMLS #O4909637

$4,290,000
09/02/2003

Sold (Public Record)

Public Record #120231079

$742,500

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 5417 Osprey Isle Lane

Taxable ValueLand-Additions-Total-
Tax Record2024$60,372 ($5,031 / month)
Home Facts
Beds6Total Finished SqFt8,260 SqFtAbove Grade Finished SqFt8,260 SqFtStories2Lot Size39,847 SqFtStyleSingle Family ResidenceYear Built2007ZoningR-1AACountyORANGEAPN21-23-28-3870-00-090Fireplace TypeHas Fireplace

Schools near 5417 Osprey Isle Lane

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Palm Lake Elementary School
Public - K to 5
Cornerstone Academy Charter
Charter - K to 8
Chain Of Lakes Middle School
Public - 6 to 8
Dr. Phillips High School
Public - 9 to 12
Rating
School
Distance
Palm Lake Elementary School
PublicK to 5

Cornerstone Academy Charter
CharterK to 8

Chain Of Lakes Middle School
Public6 to 8

Dr. Phillips High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of SOUTHERN REALTY GROUP LLC, Teresa Stewart; SOUTHERN REALTY GROUP LLC, Michael Stewart

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 11/20/2025 11:18 AM