1421 Sunnyside Drive, Maitland, FL 32751
Local realty services provided by:Better Homes and Gardens Real Estate Lifestyles Realty
Listed by: amanda binns
Office: strickland realty group inc
MLS#:O6358123
Source:MFRMLS
Price summary
- Price:$999,999
- Price per sq. ft.:$330.03
About this home
Priced below appraised value for a limited opportunity to capture instant equity.
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....
Contact an agent
Home facts
- Year built:1966
- Listing ID #:O6358123
- Added:154 day(s) ago
- Updated:April 25, 2026 at 12:39 PM
Rooms and interior
- Bedrooms:4
- Total bathrooms:3
- Full bathrooms:2
- Half bathrooms:1
- Flooring:Carpet, Ceramic Tile, Terrazzo, Wood
- Dining Description:Eat In Kitchen, Living Room/Dining Room Combo
- Kitchen Description:Dishwasher, Disposal, Eat-in Kitchen, Kitchen/Family Room Combo, Solid Surface Counters, Solid Wood Cabinets
- Bedroom Description:Primary Bedroom Main Floor, Primary Bedroom Upstairs
- Living area:2,116 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Electric
- Central air:Yes
Structure and exterior
- Roof:Shingle
- Year built:1966
- Building area:2,116 sq. ft.
- Lot area:0.31 Acres
- Lot Features:Corner Lot
- Architectural Style:Custom, Florida, Patio Home, Ranch
- Construction Materials:Block, Concrete
- Exterior Features:Covered Porch/Patio, Enclosed, Front Porch, Lighting, Patio, Porch, Private Mailbox, Rain Gutters, Rear Porch, Screened, Side Porch, Sidewalk
- Foundation Description:Slab
- Levels:1 Story
Schools
- High school:Winter Park High
- Middle school:Maitland Middle
- Elementary school:Dommerich Elem
Utilities
- Water:Public, Water Connected
- Sewer:Public, Public Sewer, Sewer Connected
Finances and disclosures
- Price:$999,999
- Price per sq. ft.:$330.03
- Tax amount:$5,513 (2024)
Features and amenities
- Appliances:Dishwasher, Disposal, Electric Water Heater, Irrigation Equipment
- Laundry features:Laundry Room
- Amenities:Cable Available, Eat-in Kitchen, Irrigation Equipment, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Natural Gas Available, Natural Gas Connected, Open Floorplan, Phone Available, Primary Bedroom Main Floor, Primary Bedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Underground Utilities, Window Treatments
- Pool features:Child Safety Fence, Heated, In Ground, Private Pool, Salt Water, Screen Enclosure
Parking
- Parking description:Attached Garage, Boat, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Guest, Parking Pad, RV Access/Parking
- Garage:Yes
- Garage spaces:2
New listings near 1421 Sunnyside Drive
- New
$1,100,000Active4 beds 4 baths3,270 sq. ft.987 Brightwater Circle, MAITLAND, FL 32751
MLS# O6401747Listed by: KELLER WILLIAMS WINTER PARK - Open Sun, 12 to 2pmNew
$485,000Active3 beds 3 baths1,652 sq. ft.245 Quayside Circle, MAITLAND, FL 32751
MLS# O6401831Listed by: KELLER WILLIAMS WINTER PARK - Open Sun, 1 to 4pmNew
$759,000Active4 beds 2 baths2,159 sq. ft.1170 Willowbrook Trail, MAITLAND, FL 32751
MLS# O6396754Listed by: KELLER WILLIAMS WINTER PARK - New
$89,000Active0.23 AcresLakewood Circle, MAITLAND, FL 32751
MLS# O6401726Listed by: STRONG FOUNDATION REALTY LLC - Open Sun, 11am to 1pmNew
$429,900Active3 beds 2 baths1,512 sq. ft.2150 Tortoise Shell Drive, MAITLAND, FL 32751
MLS# O6392895Listed by: LPT REALTY, LLC - Open Sun, 1am to 3pmNew
$525,000Active3 beds 3 baths2,702 sq. ft.2011 Michael Tiago Circle, MAITLAND, FL 32751
MLS# O6397660Listed by: WATSON REALTY CORP - Open Sun, 1 to 4pmNew
$649,900Active3 beds 3 baths2,236 sq. ft.140 Wigwam Place, MAITLAND, FL 32751
MLS# O6401560Listed by: LPT REALTY, LLC - New
$500,000Active3 beds 2 baths1,707 sq. ft.612 Green Meadow Avenue, MAITLAND, FL 32751
MLS# O6401412Listed by: FLORIDA HOME TEAM REALTY LLC - New
$719,000Active4 beds 3 baths2,676 sq. ft.1511 E Horatio Avenue, MAITLAND, FL 32751
MLS# O6401235Listed by: FLORIDA REALTY INVESTMENTS - New
$200,000Active2 beds 2 baths1,111 sq. ft.1100 Lake Shadow Circle #2307, MAITLAND, FL 32751
MLS# S5148098Listed by: KELLER WILLIAMS REALTY AT THE LAKES