MAITLAND, FL 32751 1421 SUNNYSIDE DRIVE

1421 SUNNYSIDE DRIVE MAITLAND, FL - Image 11421 SUNNYSIDE DRIVE MAITLAND, FL - Image 21421 SUNNYSIDE DRIVE MAITLAND, FL - Image 3
54 more
1421 SUNNYSIDE DRIVE MAITLAND, FL - Image 41421 SUNNYSIDE DRIVE MAITLAND, FL - Image 51421 SUNNYSIDE DRIVE MAITLAND, FL - Image 61421 SUNNYSIDE DRIVE MAITLAND, FL - Image 71421 SUNNYSIDE DRIVE MAITLAND, FL - Image 81421 SUNNYSIDE DRIVE MAITLAND, FL - Image 91421 SUNNYSIDE DRIVE MAITLAND, FL - Image 101421 SUNNYSIDE DRIVE MAITLAND, FL - Image 111421 SUNNYSIDE DRIVE MAITLAND, FL - Image 121421 SUNNYSIDE DRIVE MAITLAND, FL - Image 131421 SUNNYSIDE DRIVE MAITLAND, FL - Image 141421 SUNNYSIDE DRIVE MAITLAND, FL - Image 151421 SUNNYSIDE DRIVE MAITLAND, FL - Image 161421 SUNNYSIDE DRIVE MAITLAND, FL - Image 171421 SUNNYSIDE DRIVE MAITLAND, FL - Image 181421 SUNNYSIDE DRIVE MAITLAND, FL - Image 191421 SUNNYSIDE DRIVE MAITLAND, FL - Image 201421 SUNNYSIDE DRIVE MAITLAND, FL - Image 211421 SUNNYSIDE DRIVE MAITLAND, FL - Image 221421 SUNNYSIDE DRIVE MAITLAND, FL - Image 231421 SUNNYSIDE DRIVE MAITLAND, FL - Image 241421 SUNNYSIDE DRIVE MAITLAND, FL - Image 251421 SUNNYSIDE DRIVE MAITLAND, FL - Image 261421 SUNNYSIDE DRIVE MAITLAND, FL - Image 271421 SUNNYSIDE DRIVE MAITLAND, FL - Image 281421 SUNNYSIDE DRIVE MAITLAND, FL - Image 291421 SUNNYSIDE DRIVE MAITLAND, FL - Image 301421 SUNNYSIDE DRIVE MAITLAND, FL - Image 311421 SUNNYSIDE DRIVE MAITLAND, FL - Image 321421 SUNNYSIDE DRIVE MAITLAND, FL - Image 331421 SUNNYSIDE DRIVE MAITLAND, FL - Image 341421 SUNNYSIDE DRIVE MAITLAND, FL - Image 351421 SUNNYSIDE DRIVE MAITLAND, FL - Image 361421 SUNNYSIDE DRIVE MAITLAND, FL - Image 371421 SUNNYSIDE DRIVE MAITLAND, FL - Image 381421 SUNNYSIDE DRIVE MAITLAND, FL - Image 391421 SUNNYSIDE DRIVE MAITLAND, FL - Image 401421 SUNNYSIDE DRIVE MAITLAND, FL - Image 411421 SUNNYSIDE DRIVE MAITLAND, FL - Image 421421 SUNNYSIDE DRIVE MAITLAND, FL - Image 431421 SUNNYSIDE DRIVE MAITLAND, FL - Image 441421 SUNNYSIDE DRIVE MAITLAND, FL - Image 451421 SUNNYSIDE DRIVE MAITLAND, FL - Image 461421 SUNNYSIDE DRIVE MAITLAND, FL - Image 471421 SUNNYSIDE DRIVE MAITLAND, FL - Image 481421 SUNNYSIDE DRIVE MAITLAND, FL - Image 491421 SUNNYSIDE DRIVE MAITLAND, FL - Image 501421 SUNNYSIDE DRIVE MAITLAND, FL - Image 511421 SUNNYSIDE DRIVE MAITLAND, FL - Image 521421 SUNNYSIDE DRIVE MAITLAND, FL - Image 531421 SUNNYSIDE DRIVE MAITLAND, FL - Image 541421 SUNNYSIDE DRIVE MAITLAND, FL - Image 551421 SUNNYSIDE DRIVE MAITLAND, FL - Image 561421 SUNNYSIDE DRIVE MAITLAND, FL - Image 571421 SUNNYSIDE DRIVE MAITLAND, FL - Image 58
Presented By: STRICKLAND REALTY GROUP INC with 407-448-5068. - 407-448-5068
  • MLS# O6358123
  • 11/19/2025
  • Request Tour
  • Request Info
Disclaimer: The information contained in this listing has not been verified by Homepride Group at EXP Realty and should be verified by the buyer.
  • Beds • 4
  • Full/Half Baths • 2 / 1
  • SQFT • 2,116
  • Garage • 2

Home Details

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 electrical hookup for an RV or boat. The home has been freshly painted inside and out, includes new carpet, and reflects quality craftsmanship throughout. Enjoy quick access to Winter Park’s shops, dining, parks, and cultural offerings, along with the conveniences of Maitland living, making this home an exceptional opportunity in a highly desirable Central Florida location.
Presented By: STRICKLAND REALTY GROUP INC with 407-448-5068. - 407-448-5068

Interior Features for 1421 SUNNYSIDE DRIVE

Bedrooms

Total Bedrooms4

Bathrooms

Half Baths1
Total Baths3

Other Interior Features

LivingAreaSourcePublic Records
Air Conditioning Y/NYes
Fireplace FeaturesLiving Room
Fireplace Y/NYes
FlooringCarpet, Ceramic Tile, Terrazzo, Hardwood
Furnished Y/NUnfurnished
Heating Y/NYes
Interior AmenitiesEating Space 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
Laundry FeaturesLaundry Room
Total Stories1

General for 1421 SUNNYSIDE DRIVE

Additional Parcels Y/NNo
AppliancesDishwasher, Disposal, Electric Water Heater
Architectural StyleCustom, Florida, Other, Patio, Ranch
Attached Garage Yes
Building Area UnitsSquare Feet
Carport Y/NNo
CityMAITLAND
Construction MaterialsBlock, Concrete, Other
CoolingCentral Air
CountyOrange
DirectionsIf you're coming from I-4 West (toward downtown Orlando) Take Exit 90 for FL-414 / Maitland Blvd. Keep right at the fork to continue toward Maitland Blvd. Merge onto Maitland Blvd. Take the exit for Maitland Ave. Turn right onto N Maitland Ave. After about 1 mile, turn right onto Sandspur Rd. Turn left onto Sunnyside Dr.
Elementary SchoolDommerich Elem
Facing DirectionEast
Flood Zone CodeX
Flood Zone Code XY
Full Baths2
Garage Spaces2
Garage Y/NYes
HeatingElectric
High SchoolWinter Park High
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionMAITLAND PARK SOUTH 1/46 LOT 16
LevelsOne
Listing TermsCash, Conventional, FHA, VA Loan
Living Area UnitsSquare Feet
Lot Size Square Feet13422
Lot Size UnitsSquare Feet
MLS Area32751 - Maitland / Eatonville
Middle/Junior High SchoolMaitland Middle
Minimum Lease7 Months
New ConstructionNo
Occupancy TypeVacant
OwnershipFee Simple
Patio/Porch FeaturesCovered, Enclosed, Front Porch, Other, Patio, Porch, Rear Porch, Screened, Side Porch
Pets AllowedYes
Pool FeaturesChild Safety Fence, Heated, In Ground, Lighting, Salt Water, Screen Enclosure
Property SubtypeSingle Family Residence
Property TypeResidential
RoofShingle
STELLAR_InLawSuiteYNNo
Senior Community Y/NNo
SewerPublic Sewer
Spa FeaturesHeated, In Ground
Standard StatusActive
StatusActive
Subdivision NameMAITLAND PARK SOUTH
Tax Annual Amount5513.32
Tax Lot16
Tax Year2024
Total Rooms8
UtilitiesCable Available, Natural Gas Available, Natural Gas Connected, Other, Phone Available, Public, Sewer Connected, Sprinkler Recycled, Street Lights, Underground Utilities, Water Connected
ViewGarden, Pool
Virtual TourClick here
Virtual TourClick here
Water Access Y/NNo
Water View Y/NNo
Year Built1966
ZoningRSF-2

Exterior for 1421 SUNNYSIDE DRIVE

Building Area Total3030
Covered Spaces2
Exterior AmenitiesFrench Doors, Irrigation System, Lighting, Other, Private Entrance, Private Mailbox, Private Yard, Rain Gutters, Sidewalk, Storage
FencingVinyl
Foundation DetailsSlab
Lot FeaturesCorner Lot
Lot Size Acres0.31
Lot Size Area13422
Parking FeaturesBoat, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Guest, Other, Parking Pad, RV Parking
Private PoolYes
Road Surface TypeAsphalt, Paved
VegetationMature Landscaping, Oak Trees, Trees/Landscaped
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Steven Pugh

Broker Associate | Team Leader
Price $1,100,000
MLS#O6358123
List Date 11/19/2025
Property Type Single Family
Request Tour
Request Info
Visit My Website

Similar Properties to 1421 SUNNYSIDE DRIVE

MLS® Disclaimer

MLS Logo Copyright © MFRMLS.com All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of MFR MLS. All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

33. Required DMCA Notice

DMCA Disclaimer

The Digital Millennium Copyright Act of 1998, 17 U.S.C. §512, the DMCA, provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owners behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.