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
- 3223171-3223171
- ACREAGE & UNREC
- ALABAMA CONDO
- ALBERT LEE RIDGE ADD 02
- ALBERT LEE RIDGE FIRST ADD
- ALLISON OAKES
- ALOMA
- ALOMA BUS CENTER
- ALOMA PARK
- ALOMA TRAILS
- ANDALUCIA APTS
- ARAGON CONDO
- ART SYSTEMS CENTER
- AUTUMN GLEN
- AUTUMN GLEN PH 3
- BEAR GULLY FOREST
- BEL-AIRE PINES, UNIT TWO
- BLDG 6 UNIT 189 THE STRATFORD A WINTER PARK CONDOM
- BLK C PT REP 02
- BROOKSHIRE HEIGHTS
- BROOKSHIRE HEIGHTS 1ST ADD
- BROOKSHIRE HEIGHTS 4TH ADD
- CAMPO BELLO
- CAMWOOD SUB
- CAPENS ADD
- CAROLYN ESTATES
- CARVER TOWN
- CASA ALOMA
- CEDAR RIDGE UNIT 2
- CEDARWOOD VILLAGE 1
- CHANTILLY SUB
- CHARMONT
- CHATEAUX DU LAC
- CINNAMON SHORES
- CLOISTER GROVE REP
- CLOISTER GROVE SUB
- CLOISTERS CONDO
- COLONIES
- COMSTOCK PARK
- CONWILL ESTATES
- CORONADO TWNHMS
- CORONATION ADD
- COUNTRY LANE
- CYPRESS RESERVE
- DIXIE TERRACE
- DUBSDREAD HEIGHTS
- DYER SUSAN RESUB
- EASTBROOK SUB
- EASTBROOK SUB UNIT 05
- EASTBROOK SUB UNIT 06
- EASTBROOK SUB UNIT 13
- EASTBROOK SUB UNIT 14
- EASTBROOK SUB UNIT 15
- EASTBROOK SUB UNIT 16
- EASTBROOK SUB UNIT 8
- EASTGATE SUB
- EDGEWOOD SUB
- ENCLAVE AT ALOMA
- ENCLAVE AT HAWKS CREST
- ETHEL PARK
- FAIRBANKS PARK
- FERNBROOK TRAILS
- FERNBROOK TRAILS PH 3
- FONTAINEBLEAU
- FOREST HILLS
- FOUR SEASONS CONDO
- GALLOWAY PLACE REP
- GARDEN GROVE
- GARDEN LAKE ESTATES UNIT 3
- GEORGETOWN ESTATES
- GLENCOE SUB
- GOLDEN ROD MANOR
- GOLDENROD VILLAS CONDO
- GOLDENROD VILLAS CONDOMINIUM ASSOCIATES
- GOLFSIDE GOLF COURSE SEC 01
- GOLFSIDE SEC 03
- GOLFSIDE VILLAS CONDO
- GOLFVIEW
- GOLFVIEW HEIGHTS
- GRAYSON SQUARE
- GREEN OAKS REP
- GREEN OAKS REP 02
- GREEN OAKS REP 03
- GREENVIEW AT WINTER PINES
- H VANWIES SUB
- HENKEL ADD
- HIDDEN OAKS CONDO PH 02
- HIDDEN OAKS CONDO PH 03
- HIDDEN OAKS CONDO PH 06
- HIDDEN OAKS CONDO PH 08
- HIDDEN OAKS CONDO PH 09
- HIDDEN OAKS CONDO PH 12
- HILLS
- HOWELL ESTATES 1ST ADD
- HOWELL HEIGHTS
- HUNTINGTON COURT
- HYDE PARK
- J KRONENBERGER SUB
- KAROLINA ON KILLARNEY
- KENILWORTH ESTATES
- KENILWORTH SHORES
- KENILWORTH SHORES SEC 01
- KENILWORTH SHORES SEC 02
- KENILWORTH SHORES SEC 03
- KENILWORTH SHORES SEC 04
- KENILWORTH SHORES SEC 06
- KENILWORTH SHORES SEC 07
- KENILWORTH SHORES SECTION FOUR Y/71 LOT 21 BLK B
- KILLARNEY BAY CONDO
- KILLARNEY CIRCLE
- KILLARNEY ESTATES
- KILLARNEY SHORES
- LAKE BELL TERRACE
- LAKE FLORENCE PRESERVE
- LAKE KILLARNEY CONDO
- LAKE KILLARNEY SHORES
- LAKE KNOWLES TERRACE
- LAKE KNOWLES TERRACE ADD 02
- LAKE MONTE SUB
- LAKE SPIER XING
- LAKE VIRGINIA
- LAKE WAUNATTA VILLAGE
- LAKE WAUNATTA WOODS
- 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
- LAWNDALE
- LAWNDALE ANNEX
- LAZY OAKS CONDO
- LORDS SUB
- LOST CREEK
- LUGANO TERRACE
- LYNN HAVEN
- MAGNOLIA GARDENS SUB
- MAITLAND SHORES
- MAITLAND SHORES FIRST ADD
- MEAD GARDEN
- MEADOWS AT HAWKS CREST
- MERRIE OAKS VILLAGE PH 01
- METZINGERS ADD
- MONDRIAN/WINDER PARK TWNHMS
- NORTHWOOD TERRACE
- OAKS CONDO
- OLYMPIA HEIGHTS
- OLYMPIA HEIGHTS ANNEX
- ORANGE GROVE SUB
- ORANGE TERRACE
- ORWIN MANOR WESTMINSTER SEC
- OSCEOLA COURT
- OSCEOLA PLACE
- OSCEOLA SHORES SEC 1
- OSCEOLA SUMMIT
- PARK AIRE CONDO
- PARK GREEN
- PARK GROVE
- PARK MANOR
- PARK NORTH
- PARKLANDO
- PARKLANDO #3
- PARKLANDO 03
- PARKVIEW VILLAGE
- PARKVIEW VILLAGE CONDO
- PELICAN BAY
- PENNSYLVANIA STATION 01 CONDO
- PERLE DU LAC
- PERVIS SURVEY FOR R E
- PHILLIPS CIRCLE REP
- PINES
- PINEWOOD SUB
- PRESERVE AT HAWKS CREST
- QUARTERS AT WINTER PARK CONDO
- ROBERT DHU MACDONALD PARK
- SANCTUARY AT ALOMA
- SANDALWOOD CREEK CONDO PH 01
- SANDALWOOD CREEK CONDO PH 12
- SANDLEWOOD CREEK CONDO PH 10
- SEVILLA
- SEVILLE PARK
- SICILIAN SHORES
- SLOVAK VILLAGE
- SORENSEN HEIGHTS
- SOUTH LAKEMONT SHORES
- STANSBURY ESTATES
- STRATFORD A WINTER PARK CONDO
- STRATFORD WINTER PARK
- SUBURBAN HOMES
- SUBURBAN HOMES FIRST ADD
- SWOOPE PARK
- SYLVAN HEIGHTS
- SYLVAN LAKE SHORES
- SYLVAN PARK
- TANGERINE COURT
- TANGLEWOOD SEC 3 REP
- TANGLEWOOD SEC 4
- TEMPLE HEIGHTS
- TEMPLE TERRACE ANNEX
- TERAZZO DEL SOL CONDO ASSN INC
- THOMAS M HENKELS ADD
- TIMBERLANE SHORES
- TRINITY BAY PH 2
- TUSCANIA
- TUSCANY TERRACE
- TWIN ACRES
- URBAN GREEN 12
- VALENCIA TERRACE
- VILASA TWNHMS
- VILLAGE/WHISPERWOOD
- VILLAS OF CASSELBERRY PH 2
- VILLAS OF CASSELBERRY PH 3
- VIRGINIA HEIGHTS
- VIRGINIA HEIGHTS REP
- VISTAS AT LAKE HOWELL
- WATERFALL COVE
- WATERFALL COVE AT WINTER PARK
- WATERS EDGE AT HAWKS CREST
- WHISPERING WATERS
- WHISPERING WATERS/PHILLIPS CIRCLE REP
- WHISPERWOOD CONDO
- WINDSONG ELIZABETHS WALK 43/81
- WINDSONG PRESERVE POINT 43/76
- WINDSONG-KNOWLES PLACE
- WINDSONG-PRESERVE POINT
- WINDWARD SQUARE SEC 1
- WINDWARD SQUARE SEC 2
- WINTER GREEN
- WINTER PARK
- WINTER PARK ESTATES
- WINTER PARK GARDENS CONDO
- WINTER PARK HEIGHTS
- WINTER PARK PINES
- WINTER PARK PINES MERRIE OAKS
- WINTER PARK PINES PATIO HOMES
- WINTER PARK PINES REP
- WINTER PARK REP BLK 75
- WINTER PARK VILLAGE
- WINTER PARK VILLAS BLDG 14
- WINTER PARK VILLAS CONDO
- WINTER PARK WOODS CONDO
- WINTER WOODS UNIT 01
- WINTER WOODS UNIT 03
- WINTER WOODS UNIT 04
- WOODCREST UNIT 01
- WRENWOOD CONDO
Market Summary
Current real estate data for Multi Family in WINTER PARK as of Jul 25, 2026
4
Multi Family Listed
99
Avg DOM
450
Avg $ / SqFt
$802,750
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 CENTURY 21 Carioti agent at 2392986550.
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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 CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti 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
