$4,500,000.00 | 5 bed 7.5+ bath 5,847sqft 5,847 square feet 0.72acre lot | 421 Lakewood Dr, Winter Park, FL 32789.
Listed at Prime Holdings Inc
Email: broker@primeholdings.site
Property type | Single family |
|---|---|
Price per sqft | $770 |
Garage | 3 Cars |
Year built | 1957 |
Exquisite Lakefront Estate on Lake Osceola – Winter Park, FL
This elegant Winter Park lakefront residence offers the pinnacle of luxury lakeside living, gracefully positioned on the serene shores of Lake Osceola. Nestled on a sprawling ¾-acre lot with approximately 110 feet of private lake frontage, this estate captures breathtaking sunrises and sunsets, offering panoramic elevated views that deliver a true sense of privacy and tranquility.
🏡 Grand Entry & Elegant Interiors
Arrive in style via the circular driveway, surrounded by lush, professionally landscaped grounds. Inside, thoughtfully curated renovations—with interior styling by Wolfe-Rizor Interiors—blend timeless charm with modern luxury. Expansive windows and multiple French doors invite natural light throughout, enhancing seamless indoor-outdoor transitions.
Defined foyer entry
Formal living & dining rooms with fireplace and lake views
Library/home office with privacy and charm
Grand living room accommodates a baby grand piano
Screened lanai overlooking the lake—perfect for evening relaxation
🍽 Chef’s Kitchen & Entertaining
Designed to impress, the gourmet kitchen features:
Expansive island
Commercial-grade range
Lakeview breakfast room
Catering station for hosting at scale
🛏 Luxurious Accommodations
Primary Suite (Main Level):
Private sitting area with stunning lake views
Spa-style ensuite with dual full bathrooms
Walk-in dressing room/closet
Potential 6th Bedroom (Main Level):
Former caretaker’s quarters with separate garage entry
Upstairs Living:
Four generous guest suites
Bonus/flex rooms & sitting area for added versatility
🌴 Lakeside Outdoor Living
Step outside into a true Winter Park oasis:
Terrace for outdoor dining & entertaining
Tropical pool & sprawling lawn with retaining walls
Boathouse on private frontage
Towering cypress, oak & palm trees complete the scenic escape
🚘 Additional Features
Oversized 3-car garage
Roof replaced in 2021
Quiet, private street
Walking distance to Park Avenue & Downtown Winter Park
This rare lakefront estate blends architectural elegance with unmatched location and lifestyle, delivering a truly elevated Winter Park experience.
📞 Schedule a private tour today with Prime Holdings Inc.—Luxury at its Highest Standard.
🏠 Interior Features
🛋 Rooms & Layout
Total Rooms: 14
Room Highlights:
Living Room: 30' x 20'
Dining Room: 31' x 11'
Kitchen: 25' x 13'
Dinette: 14' x 14'
Den/Library: 16' x 12'
Media Room: 23' x 14'
Game/Recreation Room: 31' x 14'
Loft: 16' x 14'
Additional Rooms: Attic, Bonus Room, Breakfast Room, Florida Room, Family Room, Formal Dining & Living Rooms, Inside Utility, Storage Room
🛏 Bedrooms
Total Bedrooms: 5
Primary Bedroom: 26' x 20' (First Floor)
Bedrooms 1–4: Range from 11' x 10' to 18' x 18'
Split bedroom layout for privacy
🛁 Bathrooms
Total Bathrooms: 9
Full Baths: 7
Half Baths: 2
🍽 Kitchen
Location: First Floor
Appliances:
Bar Fridge, Built-In Oven
Dishwasher, Disposal
Electric Water Heater & Tankless Water Heater
Freezer, Microwave, Range + Hood, Refrigerator
Washer & Dryer
Features: Eat-in space, solid surface counters, solid wood cabinetry
🔧 Laundry
Inside, with a dedicated laundry room
🌬 Heating & Cooling
Cooling: Central Air
Heating: Central, Electric
🪟 Windows & Treatments
Blinds, Drapes, Shutters, Rods
Double Pane Windows
Custom Window Treatments Throughout
🪵 Interior Finishes
Flooring: Carpet & Wood
Ceiling Fans, Crown Molding
Built-in Features, Thermostat, Walk-in Closets
🌴 Exterior Features
🌊 Waterfront
Lake Osceola (Winter Park Chain of Lakes)
Waterfront Footage: 110 ft
Views: Stunning water views from multiple rooms
🏡 Lot & Landscaping
Lot Size: 0.72 acres | 31,500 sq. ft.
Lot Shape: Irregular, Oversized
Landscaping: Mature oaks, palms, and lush manicured vegetation
Topography: Elevated, Paved Road Frontage (publicly maintained)
🏊 Outdoor Amenities
Private Pool: Gunite, In-ground, with Lighting
Private Spa: In-ground
Patios & Porches: Covered, Front/Rear, Enclosed, Balcony
Other Features: French Doors, Rain Gutters, Irrigation System, Shade Shutters, Lighting, Private Mailbox
Fencing: Yes
🚘 Garage & Parking
Attached 3-Car Garage: 38' x 22'
Parking Features:
Circular Driveway
Bath in Garage
Oversized
On-Street
Ground Level
Split Garage
Workshop in Garage
🧱 Construction & Architecture
Detail | Info |
|---|---|
Year Built: | 1957 (Fully Renovated) |
Living Area: | 5,847 sq. ft. |
Total Area: | 8,083 sq. ft. |
Construction: | Block & Wood Frame |
Foundation: | Block, Crawlspace, Slab |
Style: | Traditional |
Levels: | 2 |
Roof: | Shingle |
Facing Direction: | Southwest |
Structure Type: | Elevated |
Condition: | Completed |
💡 Utilities & Security
Utilities: Public Water & Sewer, Electricity, Natural Gas, Cable
Other: Sprinkler Well, Underground Services
Security: Owned System, Smoke Detectors
🏫 School Zoning
Elementary: Lakemont Elementary
Middle: Maitland Middle
High: Winter Park High
📍 Directions:
From Osceola Ave, turn onto Trismen Terrace, then onto Detmar Dr. Turn left on Lakewood Dr — the home is ahead.
📈 Price History Summary
Date | Event | Price | $/SqFt | Notes |
|---|---|---|---|---|
Jan 16, 2025 | Listing Removed (Rent) | $19,950 | $3/sqft | Rental Listing |
Oct 17, 2024 | Price Decreased (Rent) | $19,950 | $3/sqft | -$2,550 |
Sep 9, 2024 | Price Decreased (Rent) | $22,500 | – | -$2,000 |
Sep 2, 2024 | Price Decreased (Sale) | $4,500,000 | $770/sqft | -$250,000 |
Aug 9, 2024 | Listed for Rent | $24,500 | $4/sqft | |
May 31, 2024 | Price Decreased | $4,750,000 | $812/sqft | -$250,000 |
Apr 11, 2024 | Relisted | $4,995,000 | $854/sqft | |
Apr 1, 2024 | Listing Removed | $4,995,000 | $854/sqft | |
Mar 10, 2024 | Relisted | $5,250,000 | $888/sqft | |
Mar 8, 2024 | Listing Removed | $5,250,000 | $888/sqft | |
Jan 15, 2024 | Relisted | $5,250,000 | $888/sqft | |
Nov 21, 2023 | Listing Removed | $5,495,000 | $940/sqft | 21 days after listing |
Oct 31, 2023 | Listed | $5,495,000 | $940/sqft | +200.11% from 2001 sale |
🏷 Historical Sales (Public Records)
Date | Event | Price | $/SqFt |
|---|---|---|---|
Jun 29, 2001 | Sold | $1,825,000 | $312/sqft |
Jun 5, 1997 | Sold | $1,105,000 | $189/sqft |
Jun 1, 1989 | Sold | $1,250,000 | $214/sqft |
Jan 1, 1984 | Sold | $435,000 | $74/sqft |
Jan 1, 1970 | Sold | $65,000 | $11/sqft |
1957 | Built | – | – |
🧾 Tax History Overview
Year | Taxes | Total Assessment |
|---|---|---|
2023 | $24,480 | $1,868,777 |
2022 | $23,192 | $1,540,560 |
2021 | $22,360 | $1,496,688 |
2020 | $22,190 | $1,475,038 |
2019 | $22,887 | $1,441,875 |
2018 | $22,782 | $1,444,990 |
2017 | $22,606 | $1,385,886 |
2016 | $22,156 | $1,357,381 |
2015 | $22,688 | $1,347,945 |
2014 | $22,887 | $1,397,247 |
2013 | $22,424 | $1,317,485 |
2012 | $21,390 | $1,295,462 |
2011 | $22,688 | $1,311,002 |
2010 | $22,424 | $1,308,955 |
2009 | $24,461 | $1,483,202 |
2008 | $27,131 | $1,694,833 |
2007 | $28,449 | $1,772,641 |
The price and tax history data displayed is obtained from public records and/or MLS feeds from the local jurisdiction.
Here is a professionally formatted Permit History Summary for the property:
📝 Permit History Overview
Date | Type of Work | Project Type | Status |
|---|---|---|---|
Sep 24, 2014 | Mechanical/HVAC Application | Mechanical Work | Issued |
Dec 18, 2002 | Swimming Pool | Electrical Work, Pool & Spa Construction | Issued |
Dec 12, 2002 | Swimming Pool | Pool & Spa Construction | Final |
Nov 6, 2002 | Residential Alterations | Paving, Driveways, Sidewalks, Residential | Final |
Nov 6, 2002 | Fence Application | Fences | Complete |
Nov 5, 2002 | Mechanical/HVAC Application | HVAC, Mechanical Work | Complete |
Oct 15, 2002 | Tree Removal Permit | Landscape | Issued |
Sep 28, 1999 | Plumbing Application | Plumbing, Sewer Laterals | Revoked |
Sep 28, 1999 | Plumbing Application | Plumbing, Sewer Laterals | Complete |
Apr 14, 1999 | Tree Removal Permit | Landscape | Issued |
Sep 18, 1998 | Fence Application | Fences | Complete |
May 27, 1998 | Re-roof | Roofing | Complete |
Apr 7, 1998 | Decking/Patio | Decks and Porches, Patios | Complete |
Oct 2, 1997 | Boathouse | Electrical Work | Complete |
Jul 8, 1997 | Mechanical/HVAC Application | HVAC, Mechanical Work | Issued |
May 21, 1997 | Electrical Application | Electrical Work | Complete |
Mar 18, 1997 | Re-roof | Roofing | Complete |
Feb 14, 1995 | Driveway Permit | Paving, Driveways, Sidewalks | Complete |
Total Recorded Permits: 18
Time Span: 1995 – 2014
The permit history displayed is obtained from public records and provided for informational purposes only. It may not represent the complete permit history for the property. Accuracy is not guaranteed.
🌍 Environmental Risk Overview
Risk Factor | Level | Details |
|---|---|---|
Flood Factor | Minimal | This property’s flood risk is not changing. |
Fire Factor | Minimal | Wildfire risk remains stable. |
Heat Factor | Severe | Experienced 5 days above 107°F this year. |
Wind Factor | Extreme | Extreme risk of severe winds over the next 30 years. |
Air Factor | Minor | Risk of poor air quality is increasing. |
Provided by First Street Foundation.
📊 Multi-Source Valuation Summary
Valuation Provider | Current Estimate | March 2020 Value | Change Since 2020 | March 2024 Estimate | Change Since 2024 |
|---|---|---|---|---|---|
Quantarium | $3,990,507 | $2,086,900 | +91.2% | $4,609,410 | –13.4% |
CoreLogic® | $4,565,600 | $2,740,900 | +66.6% | $5,122,400 | –10.9% |
Collateral Analytics | $3,174,000 | $1,943,607 | +63.3% | $5,198,000 | –38.9% |
🧠 Insights
All providers show strong growth since 2020.
Each also reflects a decline from 2024, with Collateral Analytics reporting the steepest drop at -38.9%.
