Under contract-accepting backup offers. Have you been waiting for a home on the Winter Park Chain of Lakes? Here is your chance!! Discover an unparalleled living experience on the prestigious Winter Park Chain of Lakes! Nestled on highly sought-after Alabama Drive, this exquisite two-story residence invites you to embrace a lifestyle of comfort and elegance. With 3,680 square feet of meticulously designed space, this home offers five bedrooms and three and a half baths, including a charming guest suite above the garage complete with a private bath and kitchenette – perfect for visitors or extended family. A covered front porch and a welcoming circular driveway, framed by mature trees, greet you with incredible, sweeping views of Lake Maitland, promising serene mornings and breathtaking sunsets.
Step inside and feel instantly at home as original hardwood floors guide you through a spacious foyer, where a grand staircase sets a tone of refined sophistication. The heart of this home, the kitchen, is a captivating blend of functionality and style, ready for culinary adventures. It features a generous central island with a stovetop, complemented by crisp white countertops, warm wooden cabinetry, and stainless steel appliances. A built-in oven, microwave, and a charming terracotta wine rack enhance the culinary experience. Spacious, open and roomy.
Thoughtfully designed living spaces beckon, perfect for grand entertaining or cozy, intimate gatherings. An elegant living room offers a warm ambiance with a fireplace and captivating lake views that will enchant you all day long! Another expansive living area off the kitchen showcases exposed wooden beams and rich brick tile flooring, exuding rustic charm. Large windows throughout the front of the home frame picturesque lake views, creating a serene backdrop for daily life. With a total of four fireplaces—three gas and one wood-burning—you’ll find inviting focal points throughout. A sunroom, bathed in natural light from its expansive windows and finished with cheerful brick tile flooring, provides a tranquil retreat, further enhanced by the endless windows. Enjoy casual meals in the eat-in dining room, or host memorable dinners in the formal dining room, which boasts amazing custom shelving, detailed molding, a beautiful gas fireplace, original hardwood floors and of course view of the lake.
The primary suite is a luxurious sanctuary, generously sized and anchored by stunning views of Lake Maitland and a cozy fireplace, creating an inviting sitting area within the bedroom itself. The spacious primary bathroom offers a double vanity, an updated shower, and a separate soaking tub for ultimate relaxation. In the main home, you’ll find three additional bedrooms, each offering spacious comfort and ample storage.
A truly distinctive feature of this property is the private guest suite, thoughtfully designed with one bedroom, one bath, a kitchenette, and a cozy wood-burning stove, offering comfort and privacy. This versatile space serves as the home’s fifth bedroom, providing a wonderful haven for guests.
Beyond the inviting interior, the property extends its allure to the outdoors. A private wooden dock extends onto Lake Maitland, part of the prestigious Winter Park Chain of Lakes, offering direct access to shimmering waters and endless aquatic adventures. A boathouse further enhances lakeside enjoyment. A charming patio area provides an ideal setting for outdoor leisure and entertaining amidst the verdant surroundings. Welcome home!
Step inside and feel instantly at home as original hardwood floors guide you through a spacious foyer, where a grand staircase sets a tone of refined sophistication. The heart of this home, the kitchen, is a captivating blend of functionality and style, ready for culinary adventures. It features a generous central island with a stovetop, complemented by crisp white countertops, warm wooden cabinetry, and stainless steel appliances. A built-in oven, microwave, and a charming terracotta wine rack enhance the culinary experience. Spacious, open and roomy.
Thoughtfully designed living spaces beckon, perfect for grand entertaining or cozy, intimate gatherings. An elegant living room offers a warm ambiance with a fireplace and captivating lake views that will enchant you all day long! Another expansive living area off the kitchen showcases exposed wooden beams and rich brick tile flooring, exuding rustic charm. Large windows throughout the front of the home frame picturesque lake views, creating a serene backdrop for daily life. With a total of four fireplaces—three gas and one wood-burning—you’ll find inviting focal points throughout. A sunroom, bathed in natural light from its expansive windows and finished with cheerful brick tile flooring, provides a tranquil retreat, further enhanced by the endless windows. Enjoy casual meals in the eat-in dining room, or host memorable dinners in the formal dining room, which boasts amazing custom shelving, detailed molding, a beautiful gas fireplace, original hardwood floors and of course view of the lake.
The primary suite is a luxurious sanctuary, generously sized and anchored by stunning views of Lake Maitland and a cozy fireplace, creating an inviting sitting area within the bedroom itself. The spacious primary bathroom offers a double vanity, an updated shower, and a separate soaking tub for ultimate relaxation. In the main home, you’ll find three additional bedrooms, each offering spacious comfort and ample storage.
A truly distinctive feature of this property is the private guest suite, thoughtfully designed with one bedroom, one bath, a kitchenette, and a cozy wood-burning stove, offering comfort and privacy. This versatile space serves as the home’s fifth bedroom, providing a wonderful haven for guests.
Beyond the inviting interior, the property extends its allure to the outdoors. A private wooden dock extends onto Lake Maitland, part of the prestigious Winter Park Chain of Lakes, offering direct access to shimmering waters and endless aquatic adventures. A boathouse further enhances lakeside enjoyment. A charming patio area provides an ideal setting for outdoor leisure and entertaining amidst the verdant surroundings. Welcome home!
Property Details
Price:
$5,900,000
MLS #:
O6436553
Status:
Active Under Contract
Beds:
5
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ALABAMA OAKS
Neighborhood:
32789winterpark
Listed Date:
Sep 21, 2026
Finished Sq Ft:
3,680
Total Sq Ft:
4,672
Lot Size:
32,662 sqft / 0.75 acres (approx)
Year Built:
1980
See this Listing
Schools
Interior
Appliances
Built-In Oven, Cooktop, Dishwasher, Dryer, Refrigerator, Washer
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Tile, Hardwood
Heating
Central
Interior Features
Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, PrimaryBedroom Upstairs, Split Bedroom, Walk-In Closet(s)
Laundry Features
Inside, Laundry Room
Levels
Two
Exterior
Attached Garage YN
1
Construction Materials
Wood Frame, Wood Siding
Covered Spaces
2
Direction Faces
North
Exterior Features
Lighting, Private Mailbox
Garage Spaces
2
Roof
Other
Waterfront Features
Lake – Chain of Lakes
Financial
Tax Year
2025
Taxes
$12,869
Map
Community
- Address1530 ALABAMA DRIVE WINTER PARK FL
- SubdivisionALABAMA OAKS
- CityWINTER PARK
- CountyOrange
- Zip Code32789
Subdivisions in WINTER PARK
- 3223171-3223171
- 4572 PALMETTO CONDO
- ACREAGE
- ACREAGE & UNREC
- ALABAMA CONDO
- ALBERT LEE RIDGE ADD 02
- ALBERT LEE RIDGE FIRST ADD
- ALLISON OAKES
- ALOMA
- ALOMA TRAILS
- AMBERWOOD UNIT 2
- ANDALUCIA APTS
- ARAGON CONDO
- ARROWHEAD COVE
- ART SYSTEMS CENTER
- AUTUMN GLEN PH 2
- BANKS COLONIAL ESTATES
- BEL AIRE PINES
- BEL-AIRE PINES, UNIT TWO
- BRIDGEWATER
- BRIDGEWATER PH 2
- BROOKSHIRE HEIGHTS
- BROOKSHIRE HEIGHTS 1ST ADD
- BROOKSHIRE HEIGHTS 3RD ADD
- BROOKSHIRE HEIGHTS 4TH ADDITION
- CAMPO BELLO
- CAMWOOD SUB
- CANTON AVE COTTAGES 1
- CAPENS ADD
- CAROLYN ESTATES
- CARVER TOWN
- CASA ALOMA
- CASA JARDIN CONDO
- CEDAR RIDGE UNIT 2
- CEDAR RIDGE UNIT 3
- CEDARWOOD VILLAGE 1
- CHARMONT
- CHATEAUX DU LAC
- CHEROKEE PARK
- CLOISTER GROVE REP
- CLOISTER GROVE SUB
- CLOISTERS CONDO
- COLLEGE PLACE REP
- COLONIES
- COLONIES CONDO
- COMSTOCK PARK
- CONWILL ESTATES
- CORINTHEAN/WINTER PARK CONDO
- CORONADO TWNHMS
- CORONATION ADD
- CORTLAND PARK
- COUNTRY LANE
- CYPRESS RESERVE
- DIXIE TERRACE
- DUBSDREAD HEIGHTS
- DYER SUSAN RESUB
- EASTBROOK SUB
- EASTBROOK SUB UNIT 05
- EASTBROOK SUB UNIT 06
- EASTBROOK SUB UNIT 06 2ND REP
- EASTBROOK SUB UNIT 06 REP OF PT OF BLK 14
- EASTBROOK SUB UNIT 09
- EASTBROOK SUB UNIT 10
- EASTBROOK SUB UNIT 13
- EASTBROOK SUB UNIT 15
- EASTBROOK SUB UNIT 8
- EASTGATE SUB
- EDEN POINT
- ELLNO WILLO
- ENCLAVE AT ALOMA
- ENCLAVE AT HAWKS CREST
- FAIRBANKS SHORES 5TH ADD
- FAIRBANKS SHORES FIRST ADD
- FAIRBANKS SHORES THIRD ADD
- FAIRVIEW HEIGHTS REP
- FERNBROOK TRAILS PH 3
- FLORA PARK 2ND ADD
- FLORA PARK FIRST ADD
- FLOYDS SUB
- FONTAINEBLEAU
- FOREST HILLS
- FOUR SEASONS
- FOUR SEASONS CONDO
- GALLERY AT WINTER PARK SEC 02
- GALLOWAY PLACE REP
- GARDEN ACRES 2ND REP OF BLK E
- GARDEN ACRES REP
- GARDEN LAKE ESTATES UNIT 1
- GARDEN LAKE ESTATES UNIT 2
- GEORGEANN HOMES
- GEORGETOWN ESTATES UT 1
- GLENCOE SUB
- GOLDENROD VILLAS CONDO
- GOLFSIDE SEC 03
- GOLFSIDE VILLAS CONDO
- GOLFVIEW
- GOLFVIEW HEIGHTS
- GRAYSON SQUARE
- GREEN OAKS REP 02
- GREENS/PK
- GREENVIEW AT WINTER PINES
- HAMILTON PLACE
- HAWK’S CREST
- HENKEL ADD
- HIDDEN OAKS CONDO PH 01
- HIDDEN OAKS CONDO PH 02
- HIDDEN OAKS CONDO PH 04
- HIDDEN OAKS CONDO PH 05
- HIDDEN OAKS CONDO PH 08
- HIDDEN OAKS CONDO PH 12
- HILLS
- HOWELL BRANCH WOODS
- HOWELL ESTATES 1ST ADD
- HOWELL ESTATES REP
- HOWELL FOREST
- HYDE PARK
- J KRONENBERGER SUB
- JENKINS ADD
- JUSTAMERE CAMP REP
- KAROLINA ON KILLARNEY
- KAWILLA CREST
- KENILWORTH ESTATES
- KENILWORTH SHORES SEC 02
- KENILWORTH SHORES SEC 03
- KENILWORTH SHORES SEC 04
- KENILWORTH SHORES SEC 06
- KENILWORTH SHORES SEC 07
- KILLARNEY BAY CONDO
- KILLARNEY CIRCLE
- KILLARNEY ESTATES
- KINGS COVE
- LACHEN HOUSE CONDO
- LAKE BELL TERRACE
- LAKE FLORENCE PRESERVE
- LAKE FOREST PARK
- LAKE KILLARNEY
- LAKE KILLARNEY CONDO
- LAKE KILLARNEY SHORES
- LAKE KNOWLES TERRACE
- LAKE KNOWLES TERRACE ADD 02
- LAKE SPIER CROSSING
- LAKE VIRGINIA CONDO
- LAKE WAUNATTA COVE
- LAKE WAUNATTA VILLAGE
- LAKESIDE MANOR APTS CONDO
- LAKESIDE MANOR CONDOMINIUM ASSOCIATION, INC.
- LAKEVIEW TERRACE
- LANCELOT/WINTER PARK
- LANDINGS AT HAWKS CREST
- LANDMARK WINTER PARK CONDO
- LAUREL SPGS
- LAWNDALE
- LAWNDALE ANNEX
- LORDS SUB
- LORING CHASE
- LOST CREEK
- LOT 59 HYDE PARK PB 34 PGS 38 TO 40
- LUGANO TERRACE
- MAGNOLIA GARDENS SUB
- MAGNOLIA SUB
- MAITLAND SHORES
- MAITLAND SHORES FIRST ADD
- MC INTYRE PLACE CONDO
- MEAD GARDEN
- MEADOWS AT HAWKS CREST
- MINNESOTA CONDO
- MORSELAND SUB
- NORTHWOOD – WINTER PARK OASIS
- NORTHWOOD TERRACE
- OLYMPIA HEIGHTS
- ORANGE GROVE SUB
- ORANGE TERRACE
- ORANGEWOOD PARK
- ORWIN MANOR WESTMINSTER SEC
- OSCEOLA PLACE
- OSCEOLA SHORES SEC 03
- OSCEOLA SUMMIT
- PALMER AVE LAKESIDE PROP
- PARK AIRE CONDO
- PARK GREEN
- PARK GROVE
- PARK SHORE
- PARKLANDO 03
- PARKVIEW VILLAGE
- PARKVIEW VILLAGE BLDG 3032
- PARKVIEW VILLAGE CONDO
- PARKVIEW VILLAGE CONDO BLDG 2929
- PELICAN BAY
- PHILLIPS CIRCLE REP
- PINES
- PINEWOOD
- PRESERVE AT HAWKS CREST
- RIDGE HIGH 1ST ADD
- SANCTUARY AT ALOMA
- SANCTUARY AT LAKE ANN
- SANDALWOOD CREEK CONDO PH 09
- SANDALWOOD CREEK CONDO PH 12
- SANDLEWOOD CREEK CONDO
- SEVILLA
- SEVILLE PARK
- SHORES LAKE KILLARNEY
- SHORES LAKE KILLARNEY SEC 02
- SICILIAN SHORES REP 02
- SLOVAK VILLAGE
- SPRINGVIEW
- STANSBURY ESTATES
- STRATFORD A WINTER PARK CONDO
- SUBURBAN HOMES
- SYLVAN HEIGHTS
- SYLVAN LAKE SHORES
- TAMARAK
- TANGERINE COURT
- TANGLEWOOD SEC 3 REP
- TANGLEWOOD SEC 4
- TANTUM ADD
- TEMPLE HEIGHTS
- TEMPLE TERRACE
- TEMPLE TERRACE ANNEX
- THE COLONIES CONDO
- TIMBERLANE
- TIMBERLANE SHORES
- TOWNHOMES/HARPER PLACE
- TROTTERS REP
- TUCKS KNOLL
- TWIN ACRES
- URBAN GREEN 12
- VALENCIA TERRACE
- VIA LAGO/HANGING MOSS PH 1
- VILASA TWNHMS
- VILLA VIEW PARK
- VILLAGE WINTERSET INC
- VILLAS OF CASSELBERRY PH 1
- VILLAS OF CASSELBERRY PH 3
- VIRGINIA HEIGHTS
- VIRGINIA HEIGHTS REP
- VISTAS AT LAKE HOWELL
- WATERFALL COVE
- WATERFALL COVE AT WINTER PARK
- WATERFALL COVE/WINTER PARK
- WATERS EDGE AT HAWKS CREST
- WHISPERING WATERS
- WHISPERWOOD 3
- WHISPERWOOD CONDO
- WHISPERWOOD CONDO 04
- WILLA GROVE
- WILLIAMSBURG
- WINDSONG ELIZABETHS WALK
- WINDSONG LOOKOUT LANDING 43/79
- WINDSONG PRESERVE POINT 43/76
- WINDSONG-PRESERVE POINT
- WINDWARD SQUARE SEC 1
- WINDWARD SQUARE SEC 3
- WINTER GREEN
- WINTER PARK
- WINTER PARK COMMERCE CENTER
- WINTER PARK ESTATES
- WINTER PARK FOREST 1ST ADD
- 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 PINES VILLAS
- WINTER PARK RESIDENTIAL
- WINTER PARK VILLAGE
- WINTER PARK VILLAS CONDO
- WINTER PARK WOODS CONDO
- WOODCREST UNIT 01
- WOODCREST UNIT5
- WRENWOOD CONDO
- WRENWOOD CONDOMINIUM
- WRENWOOD HEIGHTS
- WRENWOOD HEIGHTS UNIT 2
- WRENWOOD UNIT 3 3RD ADD
Market Summary
Current real estate data for Single Family in WINTER PARK as of Sep 25, 2026
317
Single Family Listed
87
Avg DOM
491
Avg $ / SqFt
$1,356,396
Avg List Price
Property Summary
- Located in the ALABAMA OAKS subdivision, 1530 ALABAMA DRIVE WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32789. It is listed for $5,900,000 and features 5 beds, 4 baths, and has approximately 3,680 square feet of living space, and was originally constructed in 1980. The current price per square foot is $1,603. The average price per square foot for Single Family listings in WINTER PARK is $491. The average listing price for Single Family in WINTER PARK is $1,356,396. To schedule a showing of MLS#o6436553 at 1530 ALABAMA DRIVE in WINTER PARK, FL, contact your CENTURY 21 Carioti agent at 2392986550.
Similar Listings Nearby
Courtesy of CHARLES RUTENBERG REALTY ORLANDO. 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. 1530 ALABAMA DRIVE
WINTER PARK, FL
