443 Lakewood Dr, Winter Park, FL 32789

PENDING $3,500,000
Breathtaking aerial view of a lakefront property with lush landscaping and direct access to the water at 443 Lakewood Dr, Winter Park, FL 32789
  • Bedrooms

    3

  • Baths

    5

  • Sq. Feet

    2803

  • Year Built

    1954

  • Days On Market

    1

  • $/SqFt

    $1,249

15 Photos

  • Breathtaking aerial view of a lakefront property with lush landscaping and direct access to the water at 443 Lakewood Dr, Winter Park, FL 32789
  • Charming one-story home featuring a large, well-manicured front lawn with mature trees and established landscaping at 443 Lakewood Dr, Winter Park, FL 32789
  • Spacious tiled back patio with white metal railing overlooking a serene lake view and mature trees at 443 Lakewood Dr, Winter Park, FL 32789
  • Inviting back patio with comfortable seating and stunning lake views, perfect for outdoor relaxation and entertaining at 443 Lakewood Dr, Winter Park, FL 32789
  • Lush backyard with mature landscaping and partial fencing, offering privacy and scenic views of the lake at 443 Lakewood Dr, Winter Park, FL 32789
  • Expansive backyard sloping down to the lakefront, featuring mature trees and lush green grass at 443 Lakewood Dr, Winter Park, FL 32789
  • Beautiful lake view from the backyard, with mature landscaping framing the waterfront at 443 Lakewood Dr, Winter Park, FL 32789
  • Picturesque waterfront with boathouse featuring a tranquil lake view, perfect for boating and watersports at 443 Lakewood Dr, Winter Park, FL 32789
  • Stunning, panoramic view of the lake, showcasing the expansive water and shoreline at 443 Lakewood Dr, Winter Park, FL 32789
  • Expansive backyard with lush green grass and mature landscaping leading to the waterfront and boat dock at 443 Lakewood Dr, Winter Park, FL 32789
  • Stunning aerial view of lakefront property with lush landscaping and a serene lake Osceola backdrop at 443 Lakewood Dr, Winter Park, FL 32789
  • Beautiful aerial view showcasing the property's prime location on Lake Osceola with mature trees at 443 Lakewood Dr, Winter Park, FL 32789
  • This aerial shows a beautiful waterfront property with dock and pool overlooking Lake Osceola at 443 Lakewood Dr, Winter Park, FL 32789
  • Incredible aerial view with Downtown Orlando and Winter Park in the distance, overlooking Lake Osceola at 443 Lakewood Dr, Winter Park, FL 32789
  • Picturesque aerial shot of luxury homes along Lake Osceola with beautiful landscaping and serene waterfront views at 443 Lakewood Dr, Winter Park, FL 32789
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Home Description

This single-story home offers serene lakefront living with approximately 95 feet of prime water frontage on beautiful Lake Osceola. Whether you enjoy watersports, boating, or simply relaxing by the water, this property can provide the true joy of lakefront living. The grandfathered boat dock provides a rare opportunity for transformation, perfect for customizing your ideal lakeside retreat. The home boasts breathtaking lake views from the primary retreat, family room, dining room, and Florida room, providing a seamless connection to nature. Upon entering, you're greeted by a spacious living room that flows effortlessly into the family room. Adjacent to the living room is a formal dining room, ideal for entertaining guests. The expansive primary retreat has dual closets. Across from the primary, a generously sized bedroom features its own ensuite bathroom. The kitchen, located off the dining room, also captures stunning views of the lake, making it a delightful space. An additional bedroom with an ensuite bathroom provides privacy and comfort, while a half bath is conveniently located near this bedroom. A second half bathroom is situated in the garage. A recent update includes a new roof installed in 2022. The property spans .61 acres, providing plenty of room for future development. Located on one of Winter Park's most beautiful streets, this home is just a short walk from the charming shops and restaurants of Park Avenue and Rollins College. Experience the best of lakeside living and the vibrant Winter Park community from this stunning property. Opportunity awaits the buyer of this gorgeous property!

  • Elementary School: Lakemont Elem
  • Middle School: Maitland Middle
  • High School: Winter Park High
  • Private Pool: False
  • Water View: Lake,Lake - Chain of Lakes
  • Water Name: LAKE OSCEOLA
  • Water Frontage: Lake
  • Water Feet: 190
  • Water Extras: Boathouse,Skiing Allowed
  • Water Access: Lake,Lake - Chain of Lakes
  • Interior Features: Eat-in Kitchen,Primary Bedroom Main Floor,Solid Wood Cabinets,Window Treatments
  • Appliances: Cooktop,Dishwasher,Disposal,Dryer,Freezer,Range,Refrigerator,Washer
  • Fireplace Desc: Living Room,Wood Burning
  • Floor Covering: Carpet,Linoleum,Tile
  • Kitchen Features: Pantry
  • Additional Rooms: Family Room,Florida Room,Formal Dining Room Separate,Formal Living Room Separate
  • Architectural Style: Ranch,Traditional
  • Exterior Features: Irrigation System,Private Mailbox,Rain Gutters,Sliding Doors
  • Exterior Contruction: Block,Brick
  • Foundation: Crawlspace,Slab
  • Front Exposure: South
  • Roof: Shingle
  • Building Sqft: 3853

Approximate Room Sizes / Descriptions

Dining Room12x14FirstCarpet
Kitchen14x12FirstLinoleum
Family Room15x23FirstTile
Living Room14x27FirstCarpet
Florida Room13x20FirstTile
Primary Bedroom16x20FirstCarpet
Bedroom 211x16FirstCarpet
Bedroom 312x13FirstCarpet
  • Attached Garage: True
  • Garage: True
  • Garage Spaces: 2
  • Garage Feature: Bath In Garage,Driveway,Garage Door Opener,On Street
  • Carport: False
  • Carport Spaces: 0
  • Air Conditioning: Central Air
  • Heating: Central,Electric
  • Utilities: BB/HS Internet Available,Cable Available,Electricity Connected,Phone Available,Public,Sewer Connected,Sprinkler Meter,Water Connected
  • Lot Sqft: 26572.00
  • Lot Dim: 120x252x95x242
  • Lot Acres: 0.6100
  • Total Acre: 1/2 to less than 1
  • Lot Num: 5
  • Senior Community: False
  • Style: Single Family Residence
  • Property Desc: Elevated
  • Location: City Limits,Landscaped,Paved
  • Building Num Floors: 1
  • Pets Allowed: Yes
  • Pet Restrictions: Reach out to the city of Winter Park for more information on rules and regulations for pets.
  • : 407-644-1234

Neighborhood

The average asking price of a 3 bedroom Winter Park home in this zip code is $921,209 (73.7% less than this home).

This home is priced at $1,249/sqft, which is 59.9% less than similar homes in the 32789 zip code.

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Financial

  • Approx Payment:$17,026*
  • Taxes:$27,245

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at (407) 967-1435 and speak with one of our real estate consultants.

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES.

443 Lakewood Dr, Winter Park FL is a single family home of 2803 sqft and is currently priced at $3,500,000 . This single family home has 3 bedrooms. A comparable home for sale at 747 Mcintyre Ave in Winter Park is listed at $1,500,000. In addition to single family homes, EasyStreet also makes it easy to find Homes, Condos, New Homes and Foreclosures in Winter Park, FL. Virginia Heights, Comstock Park and Lugano Terrace are nearby neighborhoods. MLS O6287149 has been posted on this site since 3/7/2025 (today).

2025 3/9/2025.

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