101 E Winter Park St

Off Market

101 E Winter Park St

Orlando FL 32804

2206 sq. ft.

12913 sq. ft.

Duplex

Last sold for $675,000

Chuck Ferdinandsen, last sold this property on 27 July 2026 after 122 days on market.

Overview

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 currently rented as an Airbnb. Seller will transfer current SUPERHOST Airbnb account for the property. Superhost status for over 5 years with many recurring guests.

Features

4 bedrooms

2 bathrooms

1 carspace

1 garage space

2206 sq. ft. floor area

12913 sq. ft. lot size

Duplex

Estimated Value

Based on this property and similar 4 bedroom duplexes sold in Orlando over the last 12 months, the estimated median property value of 101 E Winter Park St is $535k.

Median value

$535k

Estimated value range

$485k - $675k

Median days on market

Estimated value trend

-2%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Orlando. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 101 E Winter Park St

2026

Sold

$675,000

27 Jul 2026 by Chuck Ferdinandsen, of CHARLES RUTENBERG REALTY ORLANDO

2019

Sold

$304,000

08 Feb 2019 by Mike McGraw, of REMAX Central Realty | Milledgeville

Happy sellers in Orlando

85%

85% of sellers in Orlando reported that their sale price either exceeded or met their price expectations.

Orlando stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 4 reviews in Orlando over the last 12 months.

Local market activity for 4 bedroom duplexes in Orlando

In the last 12 months, 4 four-bedroom duplexes similar to 101 E Winter Park St, have been sold.

This represents a 25% decrease in four-bedroom duplexes sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Orlando for a market analysis.

Dusty Sutton

at KELLER WILLIAMS AT THE PARKS

(7 reviews)

Get a market analysis

Kris Santullo

at FLORIDA HOME TEAM REALTY LLC

(30 reviews)

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Heidi Pfeffer-Morgan

at Dalton Wade | Florida

(38 reviews)

Get a market analysis

Lisa Gould

at KELLER WILLIAMS WINTER PARK

(208 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Orlando

Dusty Sutton

Dusty Sutton is a recommended agent for Orlando. They have 5 local sales and collected 2 local reviews across the last 12 months.

5 (7 reviews)
2 Reviews in Orlando
5 Sales in Orlando

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Kris Santullo

Kris Santullo is a recommended agent for Orlando. They have 1 local sale and collected 2 local reviews across the last 12 months.

5 (30 reviews)
2 Reviews in Orlando
1 Sale in Orlando

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Heidi Pfeffer-Morgan

Sellers who recommend Heidi Pfeffer-Morgan have praised them for being clear communication, reliable, dedicated, great negotiation, local expert, friendly, and resourceful

5 (38 reviews)
2 Reviews in Orlando
1 Sale in Orlando

View profile

Lisa Gould

Sellers who recommend Lisa Gould have praised them for being local expert, clear communication, supportive, responsive, patient, reliable, and empathetic