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
- 147 INTERLACHEN PLACE
- ALBERT LEE RIDGE 1ST ADD
- ALBERT LEE RIDGE FIRST ADD
- ALOMA
- ALOMA PARK
- ALOMA TRAILS
- AMBERWOOD UNIT 1
- ARAGON CONDO
- ART SYSTEMS CENTER
- AUTUMN GLEN PH 2
- BANKS COLONIAL ESTATES
- BEAR GULLY FOREST
- BLDG 6 UNIT 189 THE STRATFORD A WINTER PARK CONDOM
- BRIDGEWATER
- BROOKSHIRE HEIGHTS
- BROOKSHIRE HEIGHTS 1ST ADD
- BROOKSHIRE HEIGHTS 2ND ADD
- BROOKSHIRE HEIGHTS 4TH ADD
- CAMPO BELLO
- CAPENS ADD
- CAROLYN ESTATES
- CARVER TOWN
- CASA ALOMA
- CEDARWOOD VILLAGE 1
- CHARMONT
- CHATEAUX DU LAC
- CINNAMON SHORES
- CLOISTER GROVE SUB
- CLOISTERS CONDO
- COLLEGE PLACE REP
- COLONIES
- COMSTOCK PARK
- CONWILL ESTATES
- CORONADO TWNHMS
- CORONATION ADD
- CORTLAND PARK
- COUNTRY LANE
- DIXIE TERRACE
- DUBSDREAD HEIGHTS
- EASTBROOK
- EASTBROOK SUB
- EASTBROOK SUB UNIT 03
- EASTBROOK SUB UNIT 05
- EASTBROOK SUB UNIT 06
- EASTBROOK SUB UNIT 07
- EASTBROOK SUB UNIT 11
- EASTBROOK SUB UNIT 13
- EASTBROOK SUB UNIT 14
- EASTBROOK SUB UNIT 15
- EASTBROOK SUB UNIT 8
- EASTGATE SUB
- ELLNO WILLO
- ENCLAVE AT ALOMA
- ENCLAVE AT HAWKS CREST
- FAIRBANKS PARK
- FAIRBANKS SHORES 4TH ADD
- FAIRBANKS SHORES 5TH ADD
- FERNBROOK TRAILS
- FERNBROOK TRAILS PH 3
- FONTAINEBLEAU
- FOREST HILLS
- FOUR SEASONS CONDO
- FREMAR
- GARDEN ACRES REP 02 BLK E
- GARDEN LAKE ESTATES UNIT 2
- GARDEN LAKE ESTATES UNIT 3
- GEORGEANN ESTATES
- GEORGETOWN ESTATES
- GLENCOE
- GLENCOE SUB
- GLENMOOR
- GOLDENROD VILLAS CONDO
- GOLFSIDE SEC 03
- GOLFSIDE SEC 3
- GOLFSIDE VILLAS CONDO
- GOLFVIEW
- GOLFVIEW HEIGHTS
- GRAND PINES
- GRAYSON SQUARE
- GREEN OAKS REP
- GREEN OAKS REP 02
- GREEN OAKS REP 03
- GREEN TERRACE
- GREEN TERRACE V/140 LOT 3 BLK B
- GREENVIEW AT WINTER PINES
- H VANWIES SUB
- HAMILTON PLACE
- HAWKS CREST
- HIDDEN OAKS CONDO PH 01
- HIDDEN OAKS CONDO PH 02
- HIDDEN OAKS CONDO PH 03
- HIDDEN OAKS CONDO PH 04
- HIDDEN OAKS CONDO PH 08
- HIDDEN OAKS CONDO PH 09
- HIDDEN OAKS CONDO PH 10
- HIDDEN OAKS CONDO PH 11
- HIDDEN OAKS CONDO PH 12
- HIDDEN OAKS CONDO PH 7
- HIDDEN OAKS CONDOMINIUM ASSOCIATION, INC
- HORTON AARON
- HOWELL BRANCH WOODS
- HOWELL ESTATES 1ST ADD
- HOWELL ESTATES REP
- HOWELL HEIGHTS
- HYDE PARK
- J KRONENBERGER SUB
- JUSTAMERE CAMP REP
- KAROLINA ON KILLARNEY
- KAWILLA CREST
- KENILWORTH ESTATES 1ST ADD
- KENILWORTH SHORES SEC 01
- KENILWORTH SHORES SEC 02
- KENILWORTH SHORES SEC 04
- KENILWORTH SHORES SEC 05
- KENILWORTH SHORES SEC 06
- KENILWORTH SHORES SEC 07
- KILLARNEY BAY CONDO
- KILLARNEY CIRCLE
- KILLARNEY ESTATES
- KINGS COVE
- LA CASAS DE INDIANA
- LAKE BELL TERRACE
- LAKE FLORENCE PRESERVE
- LAKE FOREST PARK
- LAKE KILLARNEY CONDO
- LAKE KILLARNEY SHORES
- LAKE KNOWLES TERRACE
- LAKE KNOWLES TERRACE ADD 02
- LAKE MONTE SUB
- LAKE VIRGINIA
- LAKE VIRGINIA PT REP
- LAKE WAUNATTA VILLAGE
- LAKE WAUNATTA WOODS
- LAKEMONT ESTATES
- LAKEMONT HEIGHTS
- LAKESIDE ESTATES
- LAKESIDE MANOR APTS CONDO
- LAKESIDE MANOR CONDOMINIUM ASSOCIATION, INC.
- LAKEVIEW TERRACE
- LANCELOT/WINTER PARK
- LANDINGS AT HAWKS CREST
- LAS CASAS DE INDIANA
- LAUREL SPGS
- LAWNDALE
- LAWNDALE ANNEX
- LAZY OAKS CONDO
- LORDS SUB
- LOST CREEK
- LUGANO TERRACE
- LYMAN AVE VILLAS 1
- MAITLAND SHORES
- MAITLAND SHORES FIRST ADD
- MEAD GARDEN
- MEADOWS AT HAWKS CREST
- METZINGERS ADD
- MONDRIAN/WINDER PARK TWNHMS
- MORSELAND SUB
- NEW ENGLAND BLDG
- NORTH GOLDENROD COMMERCE PARK
- NORTHWOOD TERRACE
- OAKCREST-516
- ORANGE TERRACE
- ORWIN MANOR STRATFORD SEC
- ORWIN MANOR WESTMINSTER SEC
- OSCEOLA PLACE
- OSCEOLA SHORES SEC 03
- OSCEOLA SHORES SEC 1
- PARK AIRE CONDO
- PARK GROVE
- PARK GROVE W/125 LOT 10 BLK D
- PARK HILL
- PARK MANOR
- PARK NORTH
- PARKLANDO
- PARKLANDO #3
- PARKLANDO 03
- PARKVIEW VILLAGE
- PARKVIEW VILLAGE CONDO BLVD 2918
- PENNSYLVANIA STATION 01 CONDO
- PERVIS SURVEY FOR R E
- PHILLIPS CIRCLE REP
- PINES
- PINEWOOD SUB
- PRESERVE AT HAWKS CREST
- QUAIL HOLLOW
- QUAIL RUN
- QUARTERS AT WINTER PARK CONDO
- REPLAT OF LTS 1 2 & 3 BROOKSIDE SUB
- ROBERT DHU MACDONALD PARK
- SANCTUARY AT ALOMA
- SANDLEWOOD CREEK CONDO PH 10
- SEVILLA
- SEVILLE PARK
- SHORES LAKE KILLARNEY SEC 02
- SICILIAN SHORES
- SICILIAN SHORES REP 02
- SLOVAK VILLAGE
- SORENSEN HEIGHTS
- SOUTH LAKEMONT SHORES
- STRATFORD A WINTER PARK CONDO
- STRATFORD WINTER PARK
- SUBURBAN HOMES
- SUBURBAN HOMES SEC 2
- SWOOPE PARK
- SYLVAN HEIGHTS
- SYLVAN HGTS
- SYLVAN LAKE SHORES
- SYLVAN PARK
- TANGLEWOOD SEC 4
- TEMPLE ESTATES
- TEMPLE TERRACE
- TEMPLE TERRACE ANNEX
- TERAZZO DEL SOL CONDO ASSN INC
- TERRAZO DEL SOL
- THE ENCLAVE WINTER PARK
- TIMBERLANE
- TIMBERLANE SHORES
- TOWNHOMES/HARPER PLACE
- TROTTERS REP
- TUSCANIA
- TUSCANY PLACE FIRST ADD
- TUSCANY TERRACE
- TWIN ACRES
- VALENCIA TERRACE
- VIA LAGO/HANGING MOSS PH 09
- VILLA VIEW PARK
- VILLAGE GREEN
- VILLAGE WINTERSET INC
- VILLAGE/WHISPERWOOD
- VILLAS OF CASSELBERRY PH 2
- VILLAS OF CASSELBERRY PH 3
- VILLAS OF CASSELBERRY PH 4
- VIRGINIA HEIGHTS
- VIRGINIA HEIGHTS REP
- VISTAS AT LAKE HOWELL
- WATERFALL COVE
- WATERFALL COVE AT WINTER PARK
- WATERFALL COVE AT WINTER PARK CONDO
- WATERFALL COVE WINTER PARK
- WATERFALL COVE/WINTER PARK
- WHISPERING WATERS/PHILLIPS CIRCLE REP
- WHISPERWOOD CONDO
- WHISPERWOOD CONDO 02
- WINDSONG ELIZABETHS WALK
- WINDSONG ELIZABETHS WALK 43/81
- WINDSONG LAKESIDE SEC 02 43/71
- WINDSONG-KNOWLES PLACE
- WINDSONG-PRESERVE POINT
- WINDWARD SQUARE SEC 1
- WINDWARD SQUARE SEC 3
- WINFLOR COURT PT REP
- WINTER GREEN
- WINTER PARK
- WINTER PARK ESTATES
- WINTER PARK ESTATES SEC 2
- WINTER PARK MANOR
- WINTER PARK OAKS
- WINTER PARK PINES
- WINTER PARK PINES MERRIE OAKS
- WINTER PARK PINES PATIO HOMES
- WINTER PARK PINES REP
- WINTER PARK PINES UNIT 17
- WINTER PARK PINES UT 5
- WINTER PARK RESIDENTIAL
- WINTER PARK REV
- WINTER PARK VILLAGE
- WINTER PARK VILLAS
- WINTER PARK VILLAS CONDO
- WINTER PARK WOODS CONDO
- WINTER WOODS UNIT 01
- WRENWOOD CONDO
- WRENWOOD HEIGHTS
- WRENWOOD HEIGHTS UNIT 2
- WRENWOOD UNIT 3 3RD ADD
- WRENWOOD UNIT 3 4TH ADD
Market Summary
Current real estate data for Multi Family in WINTER PARK as of May 18, 2026
5
Multi Family Listed
73
Avg DOM
412
Avg $ / SqFt
$730,200
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 LPT Realty agent at 813.694.8061.
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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 LPT Realty include the name of the listing broker. Neither the listing company nor LPT Realty 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
