505 Jennifer Ln

Windermere, FL 34786

$2,199,000
Price
4
Beds
3,525 Sq. Ft.
$624 / Sq. Ft.
3,525
Sq. Ft.
$624
per Sq. Ft.
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Description

Villa Casablanca | Luxury Windermere Estate on 1-Acre. Some homes are built. this was transformed. Set on a rare private acre within one of Windermere’s most privately held enclaves— this estate makes an immediate architectural statement. A circular motor court, tiered fountain, and mature canopy trees establish presence before you ever step inside. What unfolds within is architectural theater. Vaulted ceilings rise to a dramatic 14-foot peak as skylights and expansive double-pane windows flood the...Villa Casablanca | Luxury Windermere Estate on 1-Acre. Some homes are built. this was transformed. Set on a rare private acre within one of Windermere’s most privately held enclaves— this estate makes an immediate architectural statement. A circular motor court, tiered fountain, and mature canopy trees establish presence before you ever step inside. What unfolds within is architectural theater. Vaulted ceilings rise to a dramatic 14-foot peak as skylights and expansive double-pane windows flood the interiors with natural light. A sculptural chandelier crowns the volume, while a full-height stone fireplace ascends as the focal point. French glass doors frame panoramic views of the private rear oasis — pool, pergola, and mature canopy beyond — creating a seamless connection between interior grandeur and outdoor serenity. The chef’s kitchen commands attention. A grand Taj Mahal quartzite island defines the center. White oak cabinetry spans floor to ceiling. The Thor range and sculpted hood rise against a full-height stone backdrop. pot filler., Viking refrigerator. Glass pendants hover overhead -- Every finish carries presence. The scullery unfolds unexpected, elevated, and unforgettable — Deep olive custom cabinetry, textured tile, LED-lit shelving, beverage refrigeration, and layered storage make it as functional as it is striking. A split plan introduces the primary suite — vaulted, private, composed. A sculptural chandelier anchors the ceiling while tailored wall moldings define the room. Dual concealed walk-in closets preserve symmetry. The primary bath is a statement of design: matte stone soaking tub beneath clerestory light, full-height stone extending into a curbless marble shower, dual tailored vanities with brushed brass accents, and patterned marble floor grounding the space in immersive opulence. An adjoining vaulted extension captures pool views and opens to the lanai. The powder room shifts tone — charcoal paneled walls, sculptural marble sink, polished brass fittings, arched mirror, and bold tile creating a rich, moody presence. A formal office behind glass French doors offers focused productivity and polished presentation. An arched corridor leads to the secondary wing where three additional bedrooms offer privacy and versatility. One suite provides direct exterior access, functioning as a cabana retreat with its own en suite bath — ideal for guests or seamless indoor-outdoor living. Outdoors, the property transforms into a private compound. A covered veranda spans the rear with classical columns and herringbone flooring. The fully equipped summer kitchen, custom wood pergola lounge, expansive lawn, fresh sod, rear gate access, and lush landscaping offer scale impossible to replicate in today’s market. Villa Casablanca is not comparable to new construction. It is rarer. Extensively renovated inside out with a long list of brand new finishes - Roof, HVAC, Double pane windows, plumbing, pool refinish, level 5 drywall smooth finish and much more. Schedule your showing today.
  1. Listed by Ahmad Hassan, PA • Brokerage DRE #2034571 • COMPASS FLORIDA LLC
    P: (718)-641-9358 C: (718)-641-9358 ahmad.hassan@compass.com

Property Details for 505 Jennifer Lane

Subdivision Name
WINDERMERE OAKS
Township
23
Garage Spaces
3
View
Trees/Woods, Water
Waterfront
No
Furnished
Unfurnished
LISTING UPDATED: 05/10/2026 03:10 PM

Property Details for 505 Jennifer Lane

StatusActive
MLS #O6384643
Days on Market38
Taxes$7,624 / year
HOA Fees$4,000 / year
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1989
Lot Size1.00 AC / 43,566 SF
CountyOrange County
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Location

Listing Courtesy of COMPASS FLORIDA LLC, Ahmad Hassan, PA
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Building Information for 505 Jennifer Lane

Stories1Year Built1989Building Size-Lot Size1.00 AC / 43,566 SF

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$12,042 per month

30 year fixed, 6.46% Interest

Principal and Interest

$11,073

Property Taxes

$635

HOA Dues

$333

The Payment Calculator is for illustrative purposes only.

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Property Information for 505 Jennifer Lane

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 5344.0
  • Building Area Units: Square Feet
  • Community Features: Public Boat Ramp
  • Direction Faces: West
  • Directions: Head south on Apopka-Vineland Rd toward Isleworth. Continue past the Isleworth entrance, then turn right onto Jennifer Lane. 505 Jennifer Lane will be on your right.
  • Elementary School: Windermere Elem
  • Middle Or Junior School: Chain of Lakes Middle
  • High School: Olympia High
  • Mls Major Change Type: Price Decrease
  • Listing Service: Full Service
  • Road Frontage Type: Street Brick, Street Paved
  • Senior Community: No
  • Unit Number: No
  • Street Number: 505
  • Street Name: JENNIFER
  • Street Suffix: LANE
  • Street Direction Suffix: Ln
  • State: FL
  • City: WINDERMERE
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Oversized, Parking Pad
Taxes and HOA Information
  • Association Approval Required: No
  • Association Fee Includes: Maintenance Grounds
  • Association Fee Requirement: Required
  • Association Name: Stuart Atherton
  • Association: Yes
  • CDD: No
  • Tax Block: 0
  • Tax Book Number: 10-27
  • Tax Legal Description: WINDERMERE OAKS 10/27 LOT 5
  • Tax Lot: 5
  • Tax Year: 2024
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Property
Lot Information
  • Additional Parcels: No
  • Lot Features: Cul-De-Sac, City Lot, Landscaped, Near Golf Course, Oversized Lot
  • Parcel Number: 092328935400050
  • Total Acreage: 1 to less than 2
  • Water Access: Lake - Chain of Lakes
  • Water Access: Yes
  • Water Body Name: LAKE DOWN
  • Water Extras: No
  • Zoning: SFR
  • Living Area: 3525
Property and Assessments
  • Year Built Numeric: 1989
  • Flood Zone Code: X
  • Flood Zone Date: 09-25-2009
  • Flood Zone Panel: 12095C0385F
  • Homestead: No
  • New Construction: No
  • Public Survey Range: 28
  • Public Survey Section: 09
Utilities
  • Sewer: Septic Tank
  • Utilities: Electricity Connected, Street Lights, Underground Utilities
  • Water Source: Well
Interior and Exterior Features
Exterior Features
  • Construction Materials: Brick, Stucco
  • Exterior Features: French Doors, Garden, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen
  • Fencing: Fenced, Masonry
  • Foundation Details: Slab
  • Levels: One
  • Other Structures: Cabana, Outdoor Kitchen
  • Patio And Porch Features: Covered, Front Porch, Patio, Porch
  • Pool Features: In Ground, Lighting
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Shingle
  • Spa Features: In Ground
  • Spa: Yes
  • Vegetation: Mature Landscaping, Oak Trees, Trees/Landscaped
  • Waterfront Feet Total: 0
  • Number Of Stories: 1
Interior Features
  • Bedrooms Total: 4
  • Bathrooms Full: 3
  • Additional Rooms: Den/Library/Office, Inside Utility
  • Appliances: Dishwasher, Disposal, Microwave, Range, Range Hood, Refrigerator
  • Cooling: Central Air
  • Fireplace Features: Living Room, Stone, Wood Burning
  • Fireplace: Yes
  • Flooring: Engineered Hardwood, Tile
  • Heating: Central, Electric
  • Interior Features: Built-in Features, Ceiling Fan(s), Chair Rail, Dumbwaiter, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Skylight(s), Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s)
  • Laundry Features: Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
  • Living Area Source: Owner
  • Living Area Units: Square Feet
  • Room Count: 3.0
  • Water View: No
  • Window Features: Double Pane Windows
  • Bathrooms Half: 1
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 505 Jennifer Lane

DateEvent & SourcePriceAppreciation
Apr 27, 2026

Price Change

MFRMLS #O6384643

$2,199,000—
Apr 27, 2026

Listed (Active)

MFRMLS #O6384643

—
Mar 26, 2026

Pending

MFRMLS #O6384643

—
DateEvent & SourcePrice
04/27/2026

Price Change

MFRMLS #O6384643

$2,199,000
04/27/2026

Listed (Active)

MFRMLS #O6384643

—
03/26/2026

Pending

MFRMLS #O6384643

—

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

Public Records for 505 Jennifer Lane

Taxable ValueLand$180,000Additions$768,490Total$948,490
Tax Record2024$7,624 ($635 / month)
Home Facts
Beds4Total Finished SqFt3,259 SqFtAbove Grade Finished SqFt3,259 SqFtStories1Lot Size43,566 SqFtStyleSingle Family ResidenceYear Built1989ZoningSFRCountyORANGEAPN09-23-28-9354-00-050Fireplace TypeHas Fireplace

Schools near 505 Jennifer Lane

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Windermere Elementary School
Public - PK to 5
Cornerstone Academy Charter
Charter - K to 8
Chain Of Lakes Middle School
Public - 6 to 8
Cornerstone Charter Academy High School
Charter - 9 to 12
Rating
School
Distance
Windermere Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Chain Of Lakes Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 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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More information about 505 Jennifer Lane, Windermere, FL 34786

505 Jennifer Lane is a single family home for sale in Windermere, FL 34786. This property was listed for sale on February 27, 2026 by COMPASS FLORIDA LLC, it's currently listed at $2,199,000. It has been on the market for a total of 38 days and was last sold on August 3, 2025. This listing's school district is Orange County Public Schools. Nearby schools include Windermere Elementary School, Cornerstone Academy Charter and Chain Of Lakes Middle School. 505 Jennifer Lane is a 4-bed, 4-bath, 3,525 sqft single family home built in 1989.

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, Inc., its subsidiaries, affiliates and their agents and associated third parties 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, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of COMPASS FLORIDA LLC, Ahmad Hassan, PA

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: 05/10/2026 03:10 PM