Rare investment opportunity in the heart of Winter Park/Rollins College area. This turnkey, fully renovated triplex is located within one of Winter Park’s highest-demand rental corridors, just steps from Rollins College, Park Avenue, and Lake Virginia.
The property features three separate 1-bedroom, 1-bath units, each with its own private outdoor patio area, positioned on a charming brick street in one of Winter Park’s most walkable and desirable neighborhoods. The asset is being delivered with strong in-place cash flow. Current rents provide additional value-add potential, with at least one unit currently operating below market rental rates, creating an opportunity for future income growth and increased returns.
The block construction property has undergone significant capital improvements, including updated electrical panels (2019), new hot water heater (2019), new windows (2017), and a new roof (2015). Two of the three units were completely renovated in 2019, offering updated interiors while maintaining the charm and character of the surrounding neighborhood.
The front unit includes washer/dryer hookups, while the middle and rear units share a common exterior-access washer/dryer area. Utilities are currently included in the rent and have been factored into annual operating expenses.
This is a rare opportunity to acquire a stabilized multifamily asset with strong rental demand driven by proximity to Rollins College, downtown Park Avenue, dining, shopping, and employment centers throughout Winter Park.
The property features three separate 1-bedroom, 1-bath units, each with its own private outdoor patio area, positioned on a charming brick street in one of Winter Park’s most walkable and desirable neighborhoods. The asset is being delivered with strong in-place cash flow. Current rents provide additional value-add potential, with at least one unit currently operating below market rental rates, creating an opportunity for future income growth and increased returns.
The block construction property has undergone significant capital improvements, including updated electrical panels (2019), new hot water heater (2019), new windows (2017), and a new roof (2015). Two of the three units were completely renovated in 2019, offering updated interiors while maintaining the charm and character of the surrounding neighborhood.
The front unit includes washer/dryer hookups, while the middle and rear units share a common exterior-access washer/dryer area. Utilities are currently included in the rent and have been factored into annual operating expenses.
This is a rare opportunity to acquire a stabilized multifamily asset with strong rental demand driven by proximity to Rollins College, downtown Park Avenue, dining, shopping, and employment centers throughout Winter Park.
Property Details
Price:
$745,000
MLS #:
O6405857
Status:
Active
Beds:
2
Baths:
3
Type:
Multi Family
Subtype:
Triplex
Subdivision:
TROTTERS REP
Neighborhood:
32789winterpark
Listed Date:
May 8, 2026
Finished Sq Ft:
1,440
Total Sq Ft:
1,686
Lot Size:
4,898 sqft / 0.11 acres (approx)
Year Built:
1942
See this Listing
Schools
Elementary School:
Audubon Park K8
Middle School:
Audubon Park K-8
High School:
Winter Park High
Interior
Appliances
Dishwasher, Dryer, Range, Refrigerator, Washer
Cooling
Wall/Window Unit(s)
Flooring
Ceramic Tile
Heating
Wall Units / Window Unit
Interior Features
Ceiling Fan(s)
Laundry Features
Common Area, Inside, Outside
Levels
One
Exterior
Construction Materials
Block
Covered Spaces
1
Exterior Features
Fenced, Sidewalk, Storage
Lot Features
City Lot
Open Parking YN
1
Other Structures
Storage
Parking Features
Common, Driveway, Off Street
Roof
Shingle
Financial
Tax Year
2025
Taxes
$5,765
Map
Community
- Address408 HOLT AVENUE WINTER PARK FL
- SubdivisionTROTTERS REP
- CityWINTER PARK
- CountyOrange
- Zip Code32789
Subdivisions in WINTER PARK
Market Summary
Current real estate data for Multi Family in WINTER PARK as of Aug 29, 2026
7
Multi Family Listed
84
Avg DOM
408
Avg $ / SqFt
$702,843
Avg List Price
Property Summary
- Located in the TROTTERS REP subdivision, 408 HOLT AVENUE WINTER PARK FL is a Multi Family for sale in WINTER PARK, FL, 32789. It is listed for $745,000 To schedule a showing of MLS#o6405857 at 408 HOLT AVENUE in WINTER PARK, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of THE REAL ESTATE PRINCIPLE, INC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 408 HOLT AVENUE
WINTER PARK, FL
