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1421 Sunnyside Drive, Maitland, FL

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$1,100,000

($520/sqft)

List Status: Active
1421 Sunnyside Drive
Maitland, FL 32751


4 beds
2 baths
2116 living sqft
Top Features
  • View: Garden, Pool
  • Subdivision: Maitland Park South
  • Built in  1966
  • Single Family Residence
Description
One or more photo(s) has been virtually staged. HUGE PRICE IMPROVEMENT Welcome to 1421 Sunnyside Drive, Maitland, FL, a beautifully maintained 4-bedroom, 2.5-bath single-family home with a pool, located on a corner lot directly adjacent to Winter Park. While this home carries a Maitland address, it sits just steps from Winter Park homes, offering the best of both locations. This move-in-ready residence features thoughtfully designed indoor and outdoor living spaces and is zoned for the top-rated Dommerich Elementary School. From the moment you arrive, manicured landscaping and an inviting covered front porch create a warm first impression. Inside, natural light fills the home through skylights and bay windows, highlighting hardwood floors and a wood-burning fireplace. The open layout provides a seamless flow between living spaces, ideal for everyday living and entertaining. The chef’s kitchen serves as the heart of the home and features custom hardwood cabinetry, granite countertops, stainless steel appliances, a wine chiller, and a spacious breakfast island with ample seating. The kitchen opens to the main living areas, creating a functional and welcoming space. The primary suite offers a private retreat with wood floors and French doors leading directly to the porch. The ensuite bathroom includes an oversized shower with spa-style jets and customized storage. Three additional bedrooms and a full bathroom are located down a terrazzo-finished hallway and include custom upgrades. The dining area captures beautiful morning light through the bay window, while the living room features French doors that open to the outdoor living space. The private backyard oasis is designed for year-round enjoyment and includes a heated pool enclosed by a full screened deck and patio, creating a true indoor-outdoor lifestyle. Additional features include a custom built-in home office with abundant storage, a freshly refinished two-car garage, and an oversized driveway with a 30-amp elect
Property Details
Additional Information
Additional Lease Restrictions
please check county and city for any lease restrictions.
Additional Parcels YN
false
Alternate Key Folio Num
292136547300160
Appliances
Dishwasher, Disposal, Electric Water Heater
Approval Process
please check county and city
Architectural Style
Custom, Florida, Other, Patio Home, Ranch
Association YN
false
Attached Garage YN
true
Available For Lease YN
1
Bathrooms Total Integer
3
Building Area Source
Public Records
Building Area Total
3030
Building Area Total Srch SqM
281.50
Building Area Units
Square Feet
Calculated List Price By Calculated SqFt
519.85
Carport YN
false
Community Features
Street Lights
Construction Materials
Block, Concrete, Other
Cooling
Central Air
Country
US
Cumulative Days On Market
144
Current Price
1100000.00
Direction Faces
East
Elementary School
Dommerich Elem
Exterior Features
French Doors, Lighting, Other, Private Entrance, Private Mailbox, Private Yard, Rain Gutters, Sidewalk, Storage
Fencing
Vinyl
Fireplace Features
Living Room
Fireplace YN
true
Flood Zone Code
X
Flood Zone Date
2009-09-25
Flood Zone Panel
12095C0255F
Flooring
Carpet, Ceramic Tile, Terrazzo, Wood
Foundation Details
Slab
Furnished
Unfurnished
Garage Spaces
2
Garage YN
true
Heating
Electric
High School
Winter Park High
Homestead YN
1
Interior Features
Eat-in Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Other, Primary Bedroom Main Floor, PrimaryBedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Window Treatments
Internet Address Display YN
true
Internet Automated Valuation Display YN
true
Internet Consumer Comment YN
false
Internet Entire Listing Display YN
true
Laundry Features
Laundry Room
Levels
One
List AOR
Orlando Regional
Living Area Meters
196.58
Living Area Source
Public Records
Living Area Units
Square Feet
Lot Features
Corner Lot
Lot Size Acres
0.31
Lot Size Square Feet
13422
Lot Size Square Meters
1247
Middle Or Junior School
Maitland Middle
Minimum Lease
7 Months
Modification Timestamp
2026-04-15T03:07:09.308Z
New Construction YN
false
Occupant Type
Vacant
Other Equipment
Irrigation Equipment, Private Entrance, Private Yard
Ownership
Fee Simple
Parcel Number
36-21-29-5473-00-160
Patio And Porch Features
Covered, Enclosed, Front Porch, Other, Patio, Porch, Rear Porch, Screened, Side Porch
Pets Allowed
Yes
Pool Private YN
true
Postal Code Plus 4
6555
Previous List Price
1199999
Price Change Timestamp
2026-03-18T21:30:27.000Z
Public Survey Range
29
Public Survey Section
36
RATIO Current Price By Calculated SqFt
519.85
Road Surface Type
Asphalt, Paved
Roof
Shingle
Room Count
8
Senior Community YN
false
Sewer
Public Sewer
Showing Requirements
Sentri Lock Box, Appointment Only, Call Listing Agent, Lockbox, ShowingTime
Spa Features
Heated, In Ground
Status Change Timestamp
2025-11-21T11:12:17.000Z
Stories Total
1
Tax Annual Amount
5513.32
Tax Block
00
Tax Book Number
1-46
Tax Legal Description
MAITLAND PARK SOUTH 1/46 LOT 16
Tax Lot
16
Tax Year
2024
Total Acreage
1/4 to less than 1/2
Total Annual Fees
0.00
Total Monthly Fees
0.00
Township
21
Universal Property Id
US-12095-N-362129547300160-R-N
Unparsed Address
1421 SUNNYSIDE DR
Utilities
Cable Available, Natural Gas Available, Natural Gas Connected, Other, Phone Available, Public, Sewer Connected, Sprinkler Recycled, Underground Utilities, Water Connected
Vegetation
Mature Landscaping, Oak Trees, Trees/Landscaped
Water Source
Public
Waterfront YN
false
Zoning
RSF-2
Neighborhood Map
Popup

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MLS #MFRO6358123 Listing courtesy of Strickland Realty Group Inc provided by Stellar MLS.

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independent verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. The source of the listing data is as follows: Stellar MLS (updated 4/15/26 2:47 AM) |

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Winter Garden, Florida 34787

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