1518 PINEWOOD DRIVE
Winter Park, FL, 32789 $ 499,900
Bedrooms3 Baths2.0 Sq 1,197 Monthly Estimate*
$ 3,119
for $499,900 with 3 bedrooms and 2 full baths. This 1,197 square foot home was built in 1947 on a lot size of 0.19.
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.
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FeaturesGeneralSewer Septic Tank
Heating Central
Cooling Central Air
Utilities Electricity Available Electricity Connected
Roof Shingle
Zoning R-1/T/W
Construction Materials Block
Year Built 1947
Property Subtype Duplex
Tax Year 2024
Ownership Fee Simple
County Orange
New Construction false
Property Type Residential Income
Subdivision Name PINEWOOD SUB
Garage Y/N false
Status Active
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
City WINTER PARK
Senior Community Y/N false
Number Of Units Total 2
MLS Area 32789 - Winter Park
Lot Size Units Square Feet
Lot Size Square Feet 8250
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Land Lease Y/N false
Tax Annual Amount 6876.67
Additional Parcels Y/N false
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6369600
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Tax Lot 5
Legal Description PINEWOOD SUB N/9 LOT 5 BLK A (LESS E 115FT) & LOT 11 BLK A
Water Access Y/N false
Water View Y/N false
Flood Zone Code X
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InteriorInterior Amenities Ceiling Fan(s)
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N false
Laundry Features Other
Total Bedrooms 3
Total Baths 2
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ExteriorExterior Amenities Other
Water Source Public
Lot Size Area 8250
Foundation Details Slab
Number of Buildings 2
Lot Size Acres 0.19
Road Surface Type Asphalt
Private Pool false
Waterfront Y/N false
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* Excluded FeaturesList ByKeller Williams Realty At The ParksBroker
offers@hometosell.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $3,119
- Monthly Property Taxes
- $573
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbyMulti-family listings in Winter Park, FL
Average List Price $772,475
Percent of Sale Price 55%
About Winter Park, FL 31,074 Population
11% Since 2002
$ 68,913 Median Income
43.49 Median Age
21% Households with Children
Trends Information provided by ATTOM Data Solutions.
4827338 Elementary School
4827337 Middle School
Unknown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 12/27/2025 | $499,900 | | Listed Price |