1421 SUNNYSIDE DRIVE, Maitland, FL 32751

• 4 beds |
• 3 baths |
• 2,116 sqft

Property 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 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.

Listing Status:

Active

Date Added:

November 21, 2025

Data Last Updated:

February 9, 2026 at 7:22AM

Listing Office:

STRICKLAND REALTY GROUP INC : 407-448-5068

Listing Agent:

Amanda Binns : 407-448-5068

MLS ID:

O6358123

Interior

• General: Eat-in KitchenKitchen/Family Room ComboLiving Room/Dining Room ComboOpen FloorplanOtherPrimary Bedroom Main FloorPrimaryBedroom UpstairsSolid Surface CountersSolid Wood CabinetsThermostatWindow Treatments
• Appliances: DishwasherDisposalElectric Water Heater
• Laundry: Laundry Room
• Flooring: CarpetCeramic TileTerrazzoWood
• A/C: Central Air
• Heating: Electric
• Fireplace: Living RoomFireplace

Exterior

• General: French DoorsLightingOtherPrivate EntrancePrivate MailboxPrivate YardRain GuttersSidewalkStorageHeatedIn Ground
• Style: CustomFloridaOtherPatio HomeRanch
• Other Structures: EnclosedPorchFront PorchRear PorchScreenedPatioSide PorchCoveredOther
• Pool: Child Safety FenceHeatedIn GroundLightingSalt WaterScreen Enclosure
• Parking: BoatDrivewayGarage Door OpenerGarage Faces RearGolf Cart ParkingGuestOtherParking PadRV Access/Parking

Construction

• Roofing: Shingle
• General: BlockConcreteOtherOneSlab

Location

• Road/Access: AsphaltPaved
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: RSF-2MAITLAND PARK SOUTH 1/46 LOT 1636-21-29-5473-00-160
• View: GardenPool
• Fencing: Vinyl

Utilities

• Utilities: Cable AvailableNatural Gas AvailableNatural Gas ConnectedOtherPhone AvailablePublicSewer ConnectedSprinkler RecycledUnderground UtilitiesWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple