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$449,900 -$40,000 (-8.16%) Price Reduced

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,197 Sq. Ft.
  • Updated 2 days ago
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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 for 1518 Pinewood Dr

General

  • Price: $449,900
  • Taxes: $6,876 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6369571
  • Updated: 1/13/2026
  • Added to Site: 20 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 5
  • Interior Features: Ceiling Fan(s), Kitchen and Family Room Combination
  • Appliances: Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full 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
  • Direction Faces: North

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

  • Exterior Const.: Block
  • Roof: Shingle
  • Stories/Levels: One
  • 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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— 1518 Pinewood Dr —

  • Keller Williams Realty At The Parks

  • Keller Williams Realty At The Parks

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1518 Pinewood Dr

School District:Orange County School District
NameGradesDistance
Princeton Elementary School
311 West Princeton Street, Orlando, FL 32804
K-50.9 mi
College Park Middle School
1201 Maury Road, Orlando, FL 32804
6-81.3 mi
Edgewater High School
3100 Edgewater Drive, Orlando, FL 32804
9-121.1 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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
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
Get Price Alerts and Save Property
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 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
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Keller Williams Realty At The Parks

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1518 Pinewood Drive, Winter Park, FL 32789 (MLS# O6369571) is a Single Family property with 3 bedrooms and 2 full bathrooms. 1518 Pinewood Drive is currently listed for $449,900 and was received on December 26, 2025. Want to learn more about 1518 Pinewood Drive? Do you have questions about finding other Single Family 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.

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