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441 Courtlea Oaks Boulevard, Winter Garden, FL 34787

$1,375,000

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Property Description

One or more photo(s) has been virtually staged. One of the largest homes in the highly desirable Courtlea Oaks community, this spacious 5-bedroom, 4.5-bath pool home offers over 4,000 square feet of living space and an exceptional opportunity in the heart of Winter Garden's golf cart district.The flexible floor plan includes a rare apartment above the garage connected to the main home, providing ideal space for guests, extended family, a private office, or additional living quarters.Important updates have already been completed by these original to the home owners, including a new roof and A/C systems installed just two years ago, offering peace of mind for the next owner. Step outside to enjoy a beautiful pool and a private setting backing to the West Orange Trail, perfect for biking, walking, and outdoor recreation right from your backyard.Located just minutes from historic downtown Winter Garden, residents enjoy boutique shopping, dining, breweries, and the award-winning Saturday Farmers Market, along with numerous festivals and community events throughout the year.With its generous square footage, versatile layout, and unbeatable location, homes like this rarely come available in Courtlea Oaks.

441 Courtlea Oaks Boulevard | MLS# O6385964

This single family home located at 441 Courtlea Oaks Boulevard, Winter Garden, FL 34787 is currently listed for sale with an asking price of $1,375,000. This property was built in 2000 and has 5 bedrooms and 4 full and 1 partial baths with 4089 sq. ft. Courtlea Oaks Boulevard is located in the COURTLEA OAKS subdivision. Search COURTLEA OAKS real estate on rstein.watsonrealtycorp.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air
Fenced: Yes
Garage: 3 car attached
Heating: Central, Electric
Lot Size: 0.43 Acres
Roof Type: Shingle
Stories: 2.0
Taxes: $5,551
Year Built: 2000
Square Feet: 4,089

Amenities

Ceiling Fans(s)
Crown Molding
High Ceilings
Open Floorplan
Solid Surface Counters
Solid Wood Cabinets
Thermostat
Walk-In Closet(s)
French Doors
Outdoor Shower
Rain Gutters
Sidewalk

Feature Descriptions

Appliances: Built-In Oven, Cooktop, Dishwasher, Refrigerator
Directions: Heading South on FL-429, take exit 24 for Plant Street. Turn right onto Plant St. Turn right onto N Dillard Street. Turn right onto Courtlea Oaks Blvd. Home is on the right.
Exterior: Block, Concrete, Stucco, Frame
Fencing: Vinyl
Fireplace: Family Room
Fireplace Y/N: Yes
Flood Zone Code: X
Flooring: Carpet, Tile, Wood
Foundation: Slab
HOA Fee: 500/ Semi-Annually
HOA Y/N: Yes
Home Warranty Y/N: No
Listing Terms: Cash, Conventional, FHA, VA Loan
Lot Dimensions: 0.43
Ownership: Fee Simple
Parking: Driveway
Parking Notes: Driveway
Pets Allowed: Yes
Pets Restrictions: Please confirm any restrictions with HOA.
Pool: Gunite, In Ground, Lighting
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Sewer: Public Sewer
Showing Instructions: Appointment Only, Call Listing Agent, See Remarks
Spa: In Ground
Special Sale Provisions: None
Swimming Pool: Yes
Utilities: Cable Available, Electricity Connected, Public, Water Connected
Water: Public
Water Access Y/N: No
Zoning: R-1

Room Sizes

Kitchen: 11x10
Great Room: 27x18
Primary Bedroom: 18x13

Local Schools

High School: West Orange High
Middle School: Lakeview Middle
Elementary School: Tildenville Elem

Listed By / Shown By

Listed By

Agency Name: LAKESIDE REALTY WINDERMERE INC
Agency Contact: 407-876-5575

Shown By

Agent Name: Bob Stein
Agent Phone: (386) 843-3304
Agency Title: Watson Realty Corp., REALTORS ®

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Estimated Payment

$ 7,494.08 per month $6,630.46 Principal & Interest $462.58 Property Tax $401.04 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 03/05/2026. The listing information on this page last changed on 03/05/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 03/05/2026 3:07:08 AM EST) or GAMLS (last updated Wed 03/04/2026 11:15:00 PM EST) or Stellar MLS (last updated Thu 03/05/2026 1:58:49 AM EST) or SPC MLS (last updated Wed 03/04/2026 11:20:38 PM EST) or Martin MLS (last updated Wed 03/04/2026 11:38:12 PM EST) or Indian River MLS (last updated Wed 03/04/2026 11:30:24 PM EST) or Daytona MLS (last updated Wed 03/04/2026 11:36:48 PM EST) or Northeast Florida MLS (last updated Thu 03/05/2026 12:18:40 AM EST) or Beaches MLS (last updated Thu 03/05/2026 2:35:52 AM EST) or BORMLS (last updated Wed 03/04/2026 11:15:45 PM EST) or Golden Isles MLS (last updated Wed 03/04/2026 11:26:34 PM EST) or Amelia/Nassau MLS (last updated Wed 03/04/2026 11:25:17 PM EST) or Dixie Gilchrist Levy MLS (last updated Wed 03/04/2026 11:42:25 PM EST). Real estate listings held by brokerage firms other than Watson Realty Corp., REALTORS ® may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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