1421 Sunnyside Drive Maitland, FL 32751
For Sale MLS# O6358123
4 beds 3 baths 2,116 sq ft Single Family
Details for 1421 Sunnyside Drive
MLS# O6358123
Description for 1421 Sunnyside Drive, Maitland, FL, 32751
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 Information
Property Type: Residential, Single Family Residence
Status: Active
Bedrooms: 4
Bathrooms: 3
Lot Size: 0.31 Acres
Square Feet: 2,116 sq ft
Year Built: 1966
Garage: Yes
Stories: 1 Story
Construction: Block,Other,Concrete
Subdivision: Maitland Park South
Foundation: Slab
County: Orange
School Information
Elementary: Dommerich Elem
Middle: Maitland Middle
High: Winter Park High
Room Information
Main Floor
Primary Bathroom: 9.5x14.2
Living Room: 20x16
Dining Room: 23x20
Kitchen: 13x20
Bedroom 4: 11x11
Bedroom 3: 13x10
Bedroom 2: 14x11
Primary Bedroom: 12.1x17
Bathrooms
Full Baths: 2
1/2 Baths: 1
Additonal Room Information
Laundry: Laundry Room
Interior Features
Appliances: Dishwasher, Disposal, Electric Water Heater
Flooring: Carpet,Ceramic Tile,Terrazzo,Wood
Doors/Windows: Window Treatments
Fireplaces: Living Room
Additional Interior Features: Eat-In Kitchen, Other, Window Treatments, Living/Dining Room, Solid Surface Counters, Wood Cabinets, Main Level Primary, Upper Level Primary, Kitchen/Family Room Combo, Open Floorplan, Built-in Features
Utilities
Water: Public
Sewer: Public Sewer
Other Utilities: Cable Available,Natural Gas Available,Natural Gas Connected,Municipal Utilities,Other,Phone Available,Sewer Connected,Underground Utilities,Water Connected
Cooling: Central Air
Heating: Electric
Exterior / Lot Features
Attached Garage: Attached Garage
Garage Spaces: 2
Parking Description: Golf Cart Garage, Guest, RV Access/Parking, Garage Door Opener, driveway, Other, Garage, Garage Faces Rear, Boat, Parking Pad
Roof: Shingle
Pool: In Ground, Salt Water, Screen Enclosure, Heated, Other
Lot View: Garden,Pool
Fencing: Vinyl
Additional Exterior/Lot Features: French Patio Doors, Private Yard, Private Entrance, Rain Gutters, Sprinkler/Irrigation, Lighting, Other, Storage, Other, Patio, Porch, Covered, Enclosed, Screened, Rear Porch, Side Porch, Front Porch, Corner Lot, Landscaped
Community Features
Community Features: Sidewalks, Street Lights
Driving Directions
If 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.
Financial Considerations
Terms: Cash,Conventional,FHA,VA Loan
Tax/Property ID: 36-21-29-5473-00-160
Tax Amount: 5513.32
Tax Year: 2024
A broker reciprocity listing courtesy: STRICKLAND REALTY GROUP INC
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Interest rate and annual percentage rate (APR) are based on current market conditions, are for informational purposes only, are subject to change without notice and may be subject to pricing add-ons related to property type, loan amount, loan-to-value, credit score and other variables. Estimated closing costs used in the APR calculation are assumed to be paid by the borrower at closing. If the closing costs are financed, the loan, APR and payment amounts will be higher. If the down payment is less than 20%, mortgage insurance may be required and could increase the monthly payment and APR. Contact us for details. Additional loan programs may be available. Accuracy is not guaranteed, and all products may not be available in all borrower's geographical areas and are based on their individual situation. This is not a credit decision or a commitment to lend.
Sales History & Tax Summary for 1421 Sunnyside Drive
Sales History
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Tax Summary
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
Schools
Schools nearby 1421 Sunnyside Drive
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The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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