Some properties check a box. This one opens a door.
This 3-bed, 2-bath home in the heart of Winter Garden is more than a place to live. It’s a wealth-building opportunity sitting in plain sight. The floor plan sets up beautifully for a duplex conversion: a 1/1 in the front and a 2/1 in the back. Live in one side and let your tenant cover the mortgage, or rent both and start building cash flow from day one.
At approximately 1,184 sq ft, the footprint is manageable, the concept is proven, and the location makes it work. You’re minutes from historic downtown Winter Garden, major shopping corridors, top dining, and highway access. The kind of address that attracts reliable tenants and holds long-term value in one of Orange County’s strongest markets.
House hacking, buy-and-hold, or straight investment play. However you run the numbers, this one makes sense.
ROOF is 2020, WATER HEATER 2021 and HVAC 2016
This 3-bed, 2-bath home in the heart of Winter Garden is more than a place to live. It’s a wealth-building opportunity sitting in plain sight. The floor plan sets up beautifully for a duplex conversion: a 1/1 in the front and a 2/1 in the back. Live in one side and let your tenant cover the mortgage, or rent both and start building cash flow from day one.
At approximately 1,184 sq ft, the footprint is manageable, the concept is proven, and the location makes it work. You’re minutes from historic downtown Winter Garden, major shopping corridors, top dining, and highway access. The kind of address that attracts reliable tenants and holds long-term value in one of Orange County’s strongest markets.
House hacking, buy-and-hold, or straight investment play. However you run the numbers, this one makes sense.
ROOF is 2020, WATER HEATER 2021 and HVAC 2016
Property Details
Price:
$250,000
MLS #:
O6391395
Status:
Active
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
BAY ST PARK
Neighborhood:
34787wintergardenoakland
Listed Date:
Mar 21, 2026
Finished Sq Ft:
1,184
Total Sq Ft:
1,238
Lot Size:
6,635 sqft / 0.15 acres (approx)
Year Built:
1968
See this Listing
Schools
Elementary School:
Dillard Street Elem
Middle School:
Lakeview Middle
High School:
West Orange High
Interior
Appliances
Dishwasher, Disposal, Electric Water Heater
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Tile
Heating
Central, Electric
Interior Features
Primary Bedroom Main Floor, Thermostat
Laundry Features
Inside
Levels
One
Exterior
Architectural Style
Contemporary
Construction Materials
Block, Stucco
Direction Faces
East
Exterior Features
Sidewalk
Roof
Shingle
View
Trees/Woods
Financial
Tax Year
2025
Taxes
$1,671
Map
Community
- Address1040 MAXEY DRIVE WINTER GARDEN FL
- SubdivisionBAY ST PARK
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Subdivisions in WINTER GARDEN
- .
- 30 NORTH PARK
- ACREAGE
- ACREAGE & UNREC
- ALEXANDER RIDGE
- AMBERLEIGH 47/7
- ANNIE L BERRY SUB
- ARROWHEAD LAKES
- AVALON COVE
- AVALON ESTATES
- AVALON HILLS SUB
- AVALON RDG
- AVALON RESERVE VILLAGE 1
- AVALON RIDGE
- BAY ISLE 48 17
- BAY ST PARK
- BELLE MEADE PH 02 H
- BELLE MEADE PH 2
- BELLE MEADE-PH I B D & G
- BLACK LAKE
- BLACK LAKE PARK PH 01
- BLACK LAKE PRESERVE
- BRADFORD CREEK-PH II
- BRANDY CREEK
- BRAY J W F ADD 01
- BRONSONS LNDGS F & M
- BURCHSHIRE
- BURCHSHIRE Q/138 LOT 8 BLK B
- CAMBRIDGE CROSSING PH 01
- CANOPY OAKS PH 1
- CANOPY OAKS PHASE 1
- CARRIAGE POINTE A-I & L
- COOPER & SEWELL ADD
- COUNTRY LAKES
- COURTLEA OAKS PH 01A
- COURTLEA OAKS PH 02B
- COVINGTON CHASE
- COVINGTON CHASE PH 2A
- COVINGTON CHASE PH 2B
- COVINGTON PARK
- CROWN POINT SPGS
- CYPRESS RESERVE
- CYPRESS RESERVE PH 1
- CYPRESS RESERVE PH 2
- DANIEL CROSSING
- DANIELS COMMERCE CENTER
- DANIELS CROSSING
- DANIELS CROSSING REP
- DANIELS LANDING
- DANIELS LNDG A-J
- DEER ISLAND
- DEER ISLAND PH 02
- DEERFIELD PLACE A-G
- DEL WEBB OASIS
- DEL WEBB OASIS PH 3
- DUNBAR MANOR
- EAST BAY ESTATES
- EAST GARDEN MANOR ADD 03 REP
- EAST GARDEN MANOR SECOND ADD
- EMERALD RDG H
- ENCLAVE/HAMLIN
- ENCORE AT OVATION
- ENCORE AT OVATION – PHASE 3
- ENCORE AT OVATION PH 1
- ENCORE/OVATION PH 1
- ENCORE/OVATION PH 2
- ENCORE/OVATION PH 3
- ENCORE/OVATION PH 4B SEC 19
- ENCORE/OVATION-PH 3
- ENCORE/OVATION-PH 4B
- ESTATES AT LAKEVIEW PRESERVE
- ESTS/LAKEVIEW PRESERVE
- FOXCREST A-N & P
- FRIES WINTER GARDEN
- FULLERS LNDG B
- FULLERS XING PH 03 A-G
- G T SMITH SUB
- G T SMITH SUB 3
- GARDEN HEIGHTS
- GLENVIEW ESTATES 2ND ADD
- GLYNWOOD
- GLYNWOOD – PHASE 2 56/72 LOT 16
- GREYSTONE PH 01
- GROVE PK/STONE CREST A-E
- GROVE RES & SPA HOTEL CONDO 3
- GROVE RES & SPA HOTEL CONDO IV
- GROVE RESIDENCE & SPA HOTEL
- GROVE RESIDENCE & SPA HOTEL CONDO
- GROVE RESIDENCE & SPA HOTEL CONDO 1
- GROVE RESIDENCE & SPA HOTEL CONDO 2
- GROVE RESIDENCE & SPA HOTEL CONDO 3
- GROVE RESIDENCE & SPA HOTEL CONDO I
- GROVE RESIDENCE & SPA HOTEL CONDO II
- GROVE RESIDENCE & SPA HOTEL CONDO IL
- GROVE RESIDENCE Y SPA HOTEL CONDO II
- GROVE RESORT
- GROVE RESORT & SPA
- GROVE RESORT AND SPA
- GROVE RESORT AND SPA HOTEL
- GROVE RESORT AND SPA HOTEL CONDOMINIUM
- GROVE RESORT AND SPA HOTEL CONDOMINIUM 1
- GROVE RESORT AND SPA HOTEL CONDOMINIUM 3
- GROVE RESORT AND SPA HOTEL CONDOMINIUM U
- GROVE RESORT HOTEL AND SPA HOTEL CONDO 1
- GROVEHURST
- HAMILTON GARDENS
- HAMILTON GARDENS PH 2A & 2B
- HAMLIN POINTE
- HAMLIN RDG
- HAMLIN RESERVE
- HAMLIN RIDGE
- HARVEST AT OVATION
- HARVEST AT OVATION 112/64 LOT 142
- HARVEST/OVATION
- HARVET AT OVATION
- HAWKSMOOR
- HAWKSMOOR – PHASE 2
- HAWKSMOOR PH 1
- HAWKSMOOR PH 4
- HAWKSMOOR-PH 1
- HAWKSMOOR-PH 3
- HAWKSMOOR-PH 32
- HERITAGE/PLANT STREET
- HICKORY HAMMOCK
- HICKORY HAMMOCK PH 1B
- HICKORY HAMMOCK PH 1D
- HICKORY HAMMOCK PH 2B
- HICKORY HAMMOCK PH 2C
- HICKORY LAKE ESTATES
- HIGHLAND RDG
- HIGHLAND RDG PH 2
- HIGHLAND RIDGE
- HIGHLAND RIDGE 110/69 LOT 19
- HIGHLAND RIDGE PHASE 2
- HIGHLANDS AT SUMMERLAKE GROVES PHASE 3C
- HIGHLANDS/SUMMERLAKE GROVE PH 2
- HIGHLANDS/SUMMERLAKE GRVS PH 1
- HIGHLANDS/SUMMERLAKE GRVS PH 2
- HIGHLANDS/SUMMERLAKE GRVS PH 3
- HILLCREST
- HORIZON ISLE
- INDEPENDENCE COMMUNITY
- INDEPENDENCE, SIGNATURE LAKES
- ISLAND POINTE SUB
- ISLES/LK HANCOCK PH III
- JOE LOUIS PARK FIRST ADD
- JOHNS LAKE HOMESITES
- JOHNS LAKE POINTE
- JOHNS LAKE POINTE A & S
- K HOVNANIAN OSPREY RANCH LLC
- K HOVNANIAN WINDING BAY PRESERVE
- KING BAY
- KINGS BAY
- LAKE APOPKA SOUND PH 1
- LAKE AVALON GROVE
- LAKE AVALON GROVES
- LAKE AVALON GROVES 2ND REP
- LAKE AVALON GROVES REP
- LAKE AVALON GROVES REP 02
- LAKE AVALON GRVS 2ND REP
- LAKE AVALON HEIGHTS
- LAKE COVE POINTE PH 02
- LAKE FOREST SEC 10A
- LAKE HANCOCK PRESERVE
- LAKE ROBERTS LNDG
- LAKE ROBERTS LNDG E
- LAKE STAR AT OVATION
- LAKE VIEW ADD
- LAKESHORE PRESERVE
- LAKESHORE PRESERVE PH 1
- LAKESHORE PRESERVE PH 2
- LAKESHORE PRESERVE PH 5
- LAKESHORE PRESERVE PH 7
- LAKESIDE/HAMLIN
- LAKEVIEW POINTE/HORIZON WEST 1
- LAKEVIEW POINTE/HORIZON WEST P
- LAKEVIEW POINTE/HORIZON WEST PH 1
- LAKEVIEW PRESERVE
- LAKEVIEW PRESERVE PH 2
- LAKEVIEW PRESERVE PHASE 2
- LAKEVIEW VILLAGE ESTATES
- LATHAM PARK
- LATHAM PARK NORTH
- LATHAM PARK SOUTH
- LATHAN PARK NORTH
- LOVELESS J S ADD 01
- M C BRITT SUB 2
- MAGNOLIA WOOD
- MANNS FIRST ADD
- MCALLISTER LNDG PH 2
- MERCHANTS SUB
- MEZZANO
- MOUNTAIN PARK ORLANGE GROVES
- NORTHLAKE AT OVATION
- NORTHLAKE/OVATION PH 1
- OAK PARK AT WINTER GARDEN
- OAKGLEN ESTATES
- OAKLAND HILLS
- OAKLAND PARK
- OAKLAND PARKB
- OAKLAND PARKB-1
- OAKLAND PARKB-1B A
- OAKLAND PARKB-3
- OAKS/BRANDY LAKE
- OAKS/BRANDY LAKE 01 REP A & B
- OAKS/BRANDY LAKE O
- ORANGE COUNTY
- ORANGE COVE
- ORCHARD
- ORCHARD HILLS PH 1
- ORCHARD HILLS PH 2
- ORCHARD HILLS PH 3
- ORCHARD HILLS PH 4
- ORCHARD HILLS PH I
- ORCHARD PARK AT STILLWATER CROSSING PHASE 4
- ORCHARD PK/STILLWATER XING PH
- OSPRAY RANCH
- OSPREY RANCH
- OSPREY RANCH – PHASE 1
- OSPREY RANCH PH 1
- OSPREY RANCH-PH 1
- OVERLOOK 2 AT HAMLIN PHASE 2 AND 5
- OVERLOOK 2/HAMLIN PH 1 & 6
- OVERLOOK 2/HAMLIN PH 2 & 5
- OVERLOOK 2/HAMLIN PH 3 & 4
- OVERLOOK AT HAMLIN
- OVERSTREET CRATE
- OXFORD CHASE
- PALISADES
- PANTHER VIEW
- PARK AVE ESTATES
- PARK PLACE
- PARK PLACE/WINTER GARDEN
- PARKVIEW AT HAMLIN
- PLEASANT PARK
- QUESINBERRY SUB
- RAVENNA
- REGAL POINTE
- REGAL POINTE PH 02 47/133
- REGENCY OAKS F
- REGENCY OAKS PH 02 A-C
- RESERVE/CARRIAGE POINT PH 1
- RESERVE/CARRIAGE POINTE PH 1
- RESERVE/CARRIAGE POINTE PH 2
- ROPER RESERVE
- SANCTUARY/TWIN WATERS
- SAVANNAH RIDGE SUB
- SERENADE AT OVATION
- SERENADE/OVATION PH 1
- SHADOW LAWN
- SHOWALTER PARK
- SIGNATURE LAKE
- SIGNATURE LAKES
- SIGNATURE LAKES PARCEL 1A
- SIGNATURE LAKES PARCEL 1D
- SIGNATURE LAKES PARCEL 1D PH 2
- SIGNATURE LAKES PARCEL 1D PHASE 1
- SIGNATURE LAKES PH 02 A B H I J
- SIGNATURE LAKES PH 2
- SIGNATURE LAKES PH 2A
- SIGNATURE LAKES PH 3B-4, 3B-5
- SIGNATURE LAKES PH 3B-4, 3B-5 &
- SIGNATURE LAKES PH 3B-4, 3B-53B-
- SIGNATURE LAKES PH 3B-5 & 3B-7
- SIGNATURE LAKES PH 3B-6
- SIGNATURE LAKES PHASE 2A
- SIGNATURE LAKES PRCL 01C
- SIGNATURE LAKES, INDEPENDENCE
- SIGNATURE LKS-PCL 01A
- SIGNATURE LKS-PCL 01B
- SIGNATURE LKS-PCL 01D PH 02
- SILVER SPRINGS BUNGALOWS
- SILVERLEAF
- SILVERLEAF OAK
- SILVERLEAF OAKS
- SILVERLEAF OAKS AT HAMLIN
- SILVERLEAF OAKS AT HAMLIN PHASE 3A 115/63 LOT 446
- SILVERLEAF RESERVE
- SILVERLEAF RESERVE AT HAMLIN
- SILVERLEAF RESERVE AT HAMLIN PHASE 2A
- SILVERLEAF RESERVE BUNGALOWS
- SILVERLEAF RESERVE/HAML PH 2A
- SILVERLEAF RESERVE/HAMLIN PH 2
- SIPLIN HEIGHTS
- SOLOMON SUB
- SOUTHERN PINES
- SOUTHERN PINES CONDO
- SOUTHERN PINES CONDOMINIUM
- STANTON ESTATES
- STARLITE COMMERCE CENTER 48 137
- STERLING POINTE 48/1
- STONE CREEK 44/131
- STONE CRK
- STONE CRK A-1 & A-2
- STONEYBROOK WEST
- STONEYBROOK WEST 44/134
- STONEYBROOK WEST D
- STONEYBROOK WEST I
- STONEYBROOK WEST UNIT 7 64/68 LOT 5 BLK
- STONEYBROOK WEST UNIT 8
- STONEYBROOK WEST UT 04 48 48
- STONEYBROOK WEST UT 04 REP 49 121
- STOREY GROVE
- STOREY GROVE 32
- STOREY GROVE 50
- STOREY GROVE PH 1
- STOREY GROVE PH 1A-1
- STOREY GROVE PH 1A-2
- STOREY GROVE PH 1B-1
- STOREY GROVE PH 1B-1A
- STOREY GROVE PH 1B-2
- STOREY GROVE PH 1B-3
- STOREY GROVE PH 1B-4
- STOREY GROVE PH 2
- STOREY GROVE PH 3
- STOREY GROVE PH 4
- STOREY GROVE PH 5
- STOREY GRV PH 4
- STORY ROAD BUS PARK
- SUBURBAN SHORES
- SUBURBAN SHORES REP PT BLK 03
- SUMMERLAKE
- SUMMERLAKE GRVS
- SUMMERLAKE GRVS PH 2
- SUMMERLAKE PD PH 01A
- SUMMERLAKE PD PH 01B
- SUMMERLAKE PD PH 1A
- SUMMERLAKE PD PH 1B
- SUMMERLAKE PD PH 1B REP
- SUMMERLAKE PD PH 1B-A REP
- SUMMERLAKE PD PH 1B/REPLAT
- SUMMERLAKE PD PH 2A
- SUMMERLAKE PD PH 2A & 2B
- SUMMERLAKE PD PH 2C 2D 2E
- SUMMERLAKE PD PH 2C-2E
- SUMMERLAKE PD PH 3A
- SUMMERLAKE PD PH 3B
- SUMMERLAKE PD PH 3C
- SUMMERLAKE PD PH 4B
- SUMMERLAKE RESERVE
- THE GROVE RESORT
- THE GROVE RESORT AND SPA CONDOMINIUM
- THE PALISADES CONDOMINIUM
- TILDEN PLACE/WINTER GARDEN
- TOWNHOMES WINTER GARDEN
- TRIBUTE AT OVATION
- TUCKER OAKS
- TUCKER OAKS BLDG 113
- TUCKER OAKS CONDO PH 1
- TUCKER OAKS PH 3 BLDG 42
- TUCKER OKAS
- TUSCANY PH 02
- TWINWATERS
- TWINWATERS HOMEOWNERS’ ASSOCIATION, INC.
- VALENCIA SHORES
- VALENCIA SHORES REP
- VERDE PARK PH 1
- VILLAGE GROVE PH 01
- VILLAGE GROVE PH 02
- VININGS ADD WINTER GARDEN
- WALKERS GROVE TOWNHOMES
- WALKERS GROVE TWNHMS
- WATERLEIGH
- WATERLEIGH PH 1A
- WATERLEIGH PH 1B
- WATERLEIGH PH 1C
- WATERLEIGH PH 2A
- WATERLEIGH PH 2B
- WATERLEIGH PH 2C-1
- WATERLEIGH PH 2C-2 & 2C-3
- WATERLEIGH PH 2D
- WATERLEIGH PH 2E
- WATERLEIGH PH 3A
- WATERLEIGH PH 3B & 3C
- WATERLEIGH PH 3B 3C & 3D
- WATERLEIGH PH 4A
- WATERLEIGH PH 4B & 4C
- WATERLEIGH PHASE 4A
- WATERLEIGH PHASE 5 116/135 LOT 1
- WATERLWEIGH
- WATERMARK
- WATERMARK PH 1B
- WATERMARK PH 2B
- WATERMARK PH 2C
- WATERMARK PH 3
- WATERMARK PH 4
- WATERMARK PH 4A
- WATERSIDE
- WATERSIDE – THE STRAND
- WATERSIDE ON JOHNS LAKE
- WATERSIDE ON JOHNS LAKE PHASE 1
- WATERSIDE/JOHNS LAKE PH 1
- WATERSIDE/JOHNS LAKE PH 2A
- WATERSIDE/JOHNS LAKE PH 2C
- WATERSIDE/JOHNS LK-PH 2A
- WATERSIDE/JOHNS LK-PH 2B
- WEST LAKE HANCOCK ESTATES
- WESTCHESTER PLACE
- WESTFIELD LAKES PH 4
- WESTHAVEN AT OVATION
- WESTHAVEN/OVATION
- WESTLAKE MANOR
- WESTLAKE MANOR 1ST ADD
- WESTPOINT TWNHMS A & B
- WESTSIDE TOWNHOMES
- WESTSIDE TOWNHOMES PH 04
- WESTSIDE TOWNHOMES PH 4
- WESTSIDE TOWNHOMES-PH 05 A B & C
- WESTSIDE TWNHMS PH 02
- WESTSIDE TWNHMS PH 03
- WESTSIDE TWNHMS PH 04
- WESTSIDE TWNHMS-PH 05 A B & C
- WINCEY GROVES PHASE 2
- WINCEY GRVS PH 1
- WINCEY GRVS PH 2
- WINDING BAY PH 1B
- WINDING BAY PH 2
- WINDING BAY PH 3
- WINDING BAY PRESERVE
- WINDTREE GARDENS
- WINDTREE GARDENS CONDO PH 01
- WINDTREE GARDENS CONDO PH 03
- WINDTREE GARDENS CONDO PH 05
- WINDWARD CAY 48 125
- WINTER GARDEN SHORES
- WINTER GARDEN SHORES FIRST ADD
- WINTER GARDEN SHORES REP
- WINTER GARDEN TRLS 01-3
- WINTER GROVE
- WINTER OAKS
- WINTERMERE HARBOR
- WINTERMERE POINTE
- WINTERMERE POINTE PH 02 46/141
- WOODBRIDGE ON GREEN
- WOODBRIDGE ON THE GREEN
Market Summary
Current real estate data for Single Family in WINTER GARDEN as of Apr 28, 2026
778
Single Family Listed
110
Avg DOM
280
Avg $ / SqFt
$745,346
Avg List Price
Property Summary
- Located in the BAY ST PARK subdivision, 1040 MAXEY DRIVE WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $250,000 and features 3 beds, 2 baths, and has approximately 1,184 square feet of living space, and was originally constructed in 1968. The current price per square foot is $211. The average price per square foot for Single Family listings in WINTER GARDEN is $280. The average listing price for Single Family in WINTER GARDEN is $745,346. To schedule a showing of MLS#o6391395 at 1040 MAXEY DRIVE in WINTER GARDEN, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
Similar Listings Nearby
Courtesy of LPT REALTY, LLC. 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. 1040 MAXEY DRIVE
WINTER GARDEN, FL