by Global Lifestyle Properties

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Winter Garden 34787 Courtlea Oaks
441 COURTLEA OAKS BOULEVARD
$1,160,000
● House - Off Market

441 COURTLEA OAKS BOULEVARD

WINTER GARDEN, FL 34787
bedrooms
5 Beds
bathrooms
4 Baths, 1 Half Bath
square feet
4,001 Ft²
$6,855
Est. Monthly
$500
HOA / Fees

About This Property

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.
Unit Size
4,001 Ft²
Days on Market
102 days
Land Size
0.43 acres
Price per sqft
$300
Property Type
House
Property Taxes
$463
HOA Dues
$500
Year Built
2000

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Last updated: 4 months ago (Stellar MLS #O6385964)

Price History

Date / Event Date Event Price
Jun 15, 2026 Sold
Sold
May 10, 2026 In contract -
In contract
Apr 3, 2026 Price Decreased $1,199,900
↓ $29K (2.4%)
Price Decreased
Mar 20, 2026 Price Decreased $1,229,000
↓ $51K (4%)
Price Decreased
Mar 13, 2026 Price Decreased $1,280,000
↓ $95K (6.9%)
Price Decreased
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Property Highlights

Garage
Air Conditioning
Fireplace

Building Info

Overview

    General

  • Year Built: 2000
  • Effective Year Built: 2000
  • Building Count: 2
  • Bedroom Count: 4
  • Bathroom Count: 5
  • Full Bathrooms: 4
  • Partial Bathrooms: 5
  • Building Condition: 6
  • Building Quality: 10
  • Construction Type: 0
  • Building Style: 0
  • Exterior Walls Type: 7
  • Interior Walls Type: 3
  • Roof Shape Type: 7
  • Roof Cover Type: 3
  • Floor Count: 200
  • Living Units: 1
  • Floor Cover: 9
  • Basement Type: 0
  • Basement Area: 0
  • Garage Type: 1
  • Garage Square Area: 888
  • Parking Space Count: 4
  • Patio Type: 59
  • Porch Type: 126
  • Pool Type: 8

    Dimensions

  • Lot Size Square Feet: 18,602
  • Total Building Area: 4,870
  • Gross Building Area: 4,870
  • Building Area: 3,641
  • Building Area Measurement: L

    Heating and Cooling

  • Fireplace Count: 1
  • Air Conditioning: 1
  • Heating: 4
  • Heated Square Feet: 3,641
  • Heating Fuel Type: 2

    Utilities

  • Sewer System: 0
  • Water Service: 0

Building

  • Building Type: 0
  • Property Class: R
  • Subdivision: COURTLEA OAKS PH 2 B
  • Land Acres: 0000000427
  • Standard Land Use Code: 1001
  • County Land Use Code: 0103
  • State Land Use Code: 001
  • Legal Description 1: COURTLEA OAKS PHASE 2B 41/67 LOT 26

Neighborhood

  • School District Name: Orange County School District
  • Census Tract: 017401

Zoning

  • Zoning: R-1

Geography

  • Assessors Map Reference: 31
  • Subdivision Phase Number: 2B
  • Subdivision Tract Number: 1944
  • Parcel: 14-22-27-1944-00-260
  • Block: P
  • Lot: 26
  • Meridian: SEC 14 TWN 22S RNG 27E
  • Municipality: WINTER GARDEN
  • Latitude: 28.5698
  • Longitude: -81.575

    Address

  • Full Address: 441 Courtlea Oaks Blvd
  • Address - House Number: 441
  • Address - Street Name: Courtlea Oaks
  • Address - Suffix Type: Blvd
  • State: FL
  • City Name: Winter Garden
  • Carrier Code: C009
  • 4-Digit Zip Code: 4516
  • Zip Code: 34787

Valuation

    Tax

  • Total Area: 4,087
  • Tax Year: 2023
  • Tax Amount: $535,616
  • Tax Rate Code Area: 64-WG

    Appraisal Valuation

  • Standard Deviation: 0.154
  • Valuation Date: Jan 10, 2024
  • Confidence Score: 81
  • Final Value: 921,920
  • High Value: 1,063,972
  • Low Value: 779,867

    Market Valuation

  • Market Total Value: $682,240
  • Market Land Value: $175,000
  • Market Improvement Value: $507,240

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $376,568

    Exemptions

  • Homeowner Exemption: Yes

    Sales

  • Current Sale Recording Date: Mar 18, 1999
  • Current Sale Price:
  • Current Sale Document Type: 71

    Financing

  • First Mortgage Financing Type: FIX
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Courtlea Oaks


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Nearby Rentals

Unit for rent at 502 Dunbar Avenue, WINTER GARDEN, FL, 34787

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502 Dunbar Avenue, WINTER GARDEN, FL, 34787 Listing by Nancy Guadagnino
Unit for rent at 634 Foster Avenue, WINTER GARDEN, FL, 34787

$1,550 /mo

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  • 1 Bath
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634 Foster Avenue, WINTER GARDEN, FL, 34787 Listing by Anthony O'Reilly Brookes
Unit for rent at 720 Parkmont Place, WINTER GARDEN, FL, 34787

$3,000 /mo

  • 3 Beds
  • 2 Baths
  • 2,210 ft²
720 Parkmont Place, WINTER GARDEN, FL, 34787 Listing by Anthony O'Reilly Brookes


Frequently Asked Questions

When was property at 441 Courtlea Oaks Boulevard built and last sold?
The property at 441 Courtlea Oaks Boulevard was built in 2000 and last sold on Jan 1, 1970 for $39,500.
How much is this home worth?
The estimated value of the home located at 441 Courtlea Oaks Boulevard is $0.
What are some comparable homes to 441 Courtlea Oaks Boulevard?
There are currently no comparable homes to 441 Courtlea Oaks Boulevard.