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$425,000
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Property Description
Income-producing home with a detached in-law apartment in a prime central Orlando location - ideal for a house hack, long-term rental, or short-term rental (Airbnb allowed). The main house is a two-bedroom, one-bath residence, while the in-law apartment is a completely detached one-bedroom, one-bath unit with separate entrances and separate mailboxes, offering excellent privacy and flexibility. The in-law apartment is currently rented for $1,350/month on a month-to-month lease, providing immediate income and flexibility. The main house was previously rented for $1,850/month, demonstrating strong and proven rental history. Live in one unit and rent the other, or rent both for attractive cash flow. The main home is well maintained with neutral finishes, updated flooring, modern lighting, and a functional layout filled with natural light. A spacious deck and outdoor area provide excellent separation and privacy between the main house and the in-law unit. Major updates include a roof approximately 11 years old, HVAC approximately 6 years old, copper plumbing, and a septic system recently pumped and in great condition. A 4-point inspection is available upon request. Conveniently located minutes from Winter Park, College Park, Downtown Orlando, major hospitals, dining, I-4, International Drive, and Orlando International Airport. A rare opportunity offering location, flexibility, and multiple income strategies.
Full Property Details
Full Property Details for 1518 Pinewood Dr
General
- Price: $425,000
- Taxes: $6,876 (2024)
- Status: Active
- Type: Duplex
- Source: MidFloridaRegionalMLS
- MLS ID: O6369600
- Updated: 2/18/2026
- Added to Site: 67 day(s) ago
Interior
- Interior Features: Ceiling Fan(s)
Rooms
Bathrooms
- Total Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Other
Exterior
- Exterior Features: Other
Location
- Area: 32789 - Winter Park
- County: Orange
- Development Name: 32789 - Winter Park
- Subdivision: PINEWOOD SUB
- Driving Directions: Take Lawton Rd, Plaza Terrace Dr and Chelsea St to N Bumby Ave. Turn right onto N Bumby Ave. Turn left onto Virginia Dr. Take N Mills Ave to Norfolk Ave in Winter Park. Take Westchester Ave to Clay St. Take E Par St to Pinewood Dr. Turn right onto Pinewood Dr
Community
- Community Name: 32789 - Winter Park
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Septic Tank
- Water: Public
- Utility Description: Electricity Available, Electricity Connected
Structural Information
- # Buildings: 2
- Exterior Const.: Block
- Roof: Shingle
- Square Feet: 1,197
- Sq. Ft. Source: Public Records
- Year Built: 1947
Lot Features
- Lot Size (Acres): 0.19
- Lot Size (Sq. Ft.): 8,250
- Lot Size: 8250
- Street/Road Desc.: Asphalt
Financial Considerations
- Tax Amount: $6,876.67
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: PINEWOOD SUB N/9 LOT 5 BLK A (LESS E 115FT) & LOT 11 BLK A
- Flood Zone Info: X
- APN: 122229710001050
- Property ID: 122229710001050
- Block/Lot/Section: A
Listed by Keller Williams Realty At The Parks
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Schools
Schools serving 1518 Pinewood Dr
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Princeton Elementary School 311 West Princeton Street, Orlando, FL 32804 | K-5 | 0.9 mi |
College Park Middle School 1201 Maury Road, Orlando, FL 32804 | 6-8 | 1.3 mi |
Edgewater High School 3100 Edgewater Drive, Orlando, FL 32804 | 9-12 | 1.1 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1518 Pinewood Dr
Date
Details
Price
Change
Source
2/18/2026
Price Reduced
$425,000
-3.39%
MLS
1/29/2026
Price Reduced
$439,900
-2.22%
MLS
1/13/2026
Price Reduced
$449,900
-8.16%
MLS
1/06/2026
Price Reduced
$489,900
-2%
MLS
12/26/2025
Listed
$499,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 1518 Pinewood Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$6,877
—
$394,800
2%
2024
$6,877
14%
$386,645
18%
2023
$6,056
8%
$328,430
9%
2022
$5,593
48%
$301,822
26%
2021
$3,791
—
$239,923
-1%
2021
$3,791
80%
$241,473
66%
2019
$2,103
1%
$145,721
2%
2018
$2,076
2%
$143,004
2%
2017
$2,041
1%
$140,063
2%
2016
$2,025
-1%
$137,182
1%
2015
$2,053
-18%
$136,228
16%
2014
$2,504
15%
$117,500
10%
2013
$2,170
—
$106,818
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 1518 Pinewood Dr
1518 Pinewood Drive, Winter Park, FL 32789 (MLS# O6369600) is a Duplex property with 3 bedrooms and 0 full bathrooms. 1518 Pinewood Drive is currently listed for $425,000 and was received on December 26, 2025. Want to learn more about 1518 Pinewood Drive? Do you have questions about finding other Duplex real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

