101 E Winter Park St Orlando, FL 32804
College Park NeighborhoodEstimated payment $4,382/month
Highlights
- Wood Flooring
- Bonus Room
- Stone Countertops
- Princeton Elementary School Rated A-
- Corner Lot
- 5-minute walk to Mathews Park
About This Home
Discover this exceptional Turn-Key Duplex Investment Opportunity at 101/103 E. Winter Park Street in the highly sought out College Park District. Fully renovated duplex on a Double corner lot, ready for immediate income or owner-occupancy. Each unit features 2 bedrooms and 1 bathroom with modern finishes, bonus front rooms and inside laundry rooms for ultimate tenant convenience. Perfect for a house-hack strategy-live in one unit and Airbnb or lease the other to offset your mortgage and generate income. Both units have separate electrical and water meters simplifying management and maximizing efficiency along with a Generac generator serving both units during power outages. The property offers ample space for expansion, including the potential to add an ADU for increased rental income. The detached “as-is” GARAGE offers buyer opportunity to customize or upgrade. Conveniently located within walking distance to Advent Health, its highly attractive to healthcare professionals and long-term tenants. A versatile, income-producing property with modern upgrades, tenant-friendly amenities, and future expansion potential. One side is rented as an Airbnb. Seller will transfer current SUPERHOST Airbnb account for the property. Superhost status for over 5 years with many recurring guests.
airbnb.com/h/citycottageorlando
Listing Agent
CHARLES RUTENBERG REALTY ORLANDO Brokerage Phone: 407-622-2122 License #3446790 Listed on: 03/26/2026
Property Details
Home Type
- Multi-Family
Est. Annual Taxes
- $4,584
Year Built
- Built in 1953
Lot Details
- 12,913 Sq Ft Lot
- Lot Dimensions are 99x131
- Fenced
- Corner Lot
- Private Yard
Parking
- 1 Car Garage
- Driveway
- Off-Street Parking
Home Design
- Duplex
- Shingle Roof
- Block Exterior
Interior Spaces
- 1,742 Sq Ft Home
- Dry Bar
- Ceiling Fan
- Double Pane Windows
- Insulated Windows
- Blinds
- Bonus Room
- Crawl Space
Kitchen
- Range
- Microwave
- Stone Countertops
Flooring
- Wood
- Concrete
- Ceramic Tile
- Luxury Vinyl Tile
Bedrooms and Bathrooms
- 4 Bedrooms
- 2 Bathrooms
Laundry
- Laundry closet
- Dryer
- Washer
Outdoor Features
- Patio
- Separate Outdoor Workshop
Schools
- Princeton Elementary School
- College Park Middle School
- Edgewater High School
Utilities
- Central Heating and Cooling System
- Natural Gas Connected
- Tankless Water Heater
- Gas Water Heater
Listing and Financial Details
- Visit Down Payment Resource Website
- Legal Lot and Block 9 / B
- Assessor Parcel Number 13-22-29-3928-02-090
Community Details
Overview
- No Home Owners Association
- 2,206 Sq Ft Building
- Ivanhoe Terrace Subdivision
Building Details
- 2 Separate Electric Meters
- 2 Separate Water Meters
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2026 | $4,584 | $279,099 | -- | -- |
| 2025 | $4,584 | $279,099 | -- | -- |
| 2024 | $4,137 | $271,761 | -- | -- |
| 2023 | $4,137 | $256,410 | $0 | $0 |
| 2022 | $4,015 | $248,942 | $0 | $0 |
| 2021 | $3,947 | $241,691 | $0 | $0 |
| 2020 | $3,757 | $238,354 | $0 | $0 |
| 2019 | $4,750 | $274,881 | $189,900 | $84,981 |
| 2018 | $4,342 | $243,192 | $155,000 | $88,192 |
| 2017 | $3,918 | $208,658 | $136,000 | $72,658 |
| 2016 | $3,661 | $190,830 | $125,000 | $65,830 |
| 2015 | $3,396 | $170,180 | $110,000 | $60,180 |
| 2014 | $3,051 | $142,861 | $90,000 | $52,861 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 05/09/2026 05/09/26 | Price Changed | $750,000 | -2.6% | $431 / Sq Ft | |
| 04/28/2026 04/28/26 | Price Changed | $770,000 | -2.5% | $442 / Sq Ft | |
| 04/09/2026 04/09/26 | Price Changed | $790,000 | -2.5% | $454 / Sq Ft | |
| 03/26/2026 03/26/26 | For Sale | $810,000 | +166.4% | $465 / Sq Ft | |
| 02/08/2019 02/08/19 | Sold | $304,000 | +1.3% | $165 / Sq Ft | View Prior Sale |
| 01/14/2019 01/14/19 | Pending | -- | -- | -- | |
| 01/07/2019 01/07/19 | For Sale | $300,000 | -- | $163 / Sq Ft |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $100 | None Listed On Document | |
| Warranty Deed | $304,000 | Attorney | |
| Special Warranty Deed | -- | Attorney | |
| Interfamily Deed Transfer | -- | Attorney | |
| Trustee Deed | -- | -- |
Source: Stellar MLS
MLS Number: O6390682
APN: 13-2229-3928-02-090
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Listings courtesy of Stellar MLS as distributed by MLS GRID.
Based on information submitted to the MLS GRID
Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
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