Home in 1421 Sunnyside Dr Maitland for sale with MLS# O6358123
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.
1421 Sunnyside Dr, Maitland, FL 32751
- Price:
- $1,100,000.00
- Previous Asking Price:
- $1,199,999.00
- Original List Price:
- $1,300,000.00
- List Price per Sq Ft (Calculated, Approx.):
- $519.85
- Listing Type:
- For Sale
- Status:
- Active
- Listing Category:
- Residential
- Property Type:
- Single Family House
- MLS Number:
- O6358123
- Bedrooms:
- 4
- Bathrooms Total:
- 3
- Full Bath:
- 2
- Half Bath:
- 1
- Living Area:
- 2,116 Sqft
- Built-Up Area:
- 3,030 Sqft
- Lot Area:
- 13,422 Sqft
- Building Area Source:
- Public Records
- Living Area Source:
- Public Records
- Lot Features:
- Corner Lot
- Lot Size Acres:
- 0.31
- View from the Property:
- Pool, Garden
- Waterfront:
- No
- Private Pool
- Swimming Pool Features:
- Heated, In Ground, Salt Water, Screen Enclosure, Child Safety Fence, Lighting
- Spa Features:
- Heated, In Ground
- Furnished:
- Unfurnished
- Appliances:
- Dishwasher, Disposal, Electric Water Heater
- Interior:
- Eat-in Kitchen, Other, Kitchen/family Room Combo, Living Room/dining Room Combo, Open Floorplan, Thermostat, Window Treatments, Solid Surface Counters, Solid Wood Cabinets, Primary Bedroom Main Floor, Primarybedroom Upstairs
- Exterior:
- Lighting, Private Mailbox, Sidewalk, Rain Gutters, French Doors, Other, Storage, Private Yard, Private Entrance
- Patio and Porch:
- Patio, Porch, Screened, Covered, Front Porch, Rear Porch, Enclosed, Side Porch, Other
- Laundry:
- Laundry Room
- Fireplace
- Fireplace:
- Living Room
- Air Conditioning System:
- Central Air
- Heating System:
- Electric
- Fence:
- Vinyl
- Vegetation and Trees:
- Trees/landscaped, Mature Landscaping, Oak Trees
- Property Entrance Faces:
- East
- Other Equipment:
- Irrigation Equipment, Private Entrance, Private Yard
- Year Built:
- 1966
- Roof:
- Shingle
- Architectural Style:
- Other, Ranch, Patio Home, Florida, Custom
- Levels:
- One
- Construction Materials:
- Block, Other, Concrete
- Flooring:
- Carpet, Wood, Ceramic Tile, Terrazzo
- Number of stories:
- 1
- Foundation Details:
- Slab
- Flood Zone Code:
- X
- Homestead Property
- Tax Annual Amount:
- $5,513.32
- Tax Year:
- 2024
- Garage
- Garage Spaces:
- 2
- Attached Garage
- Parking Features:
- Driveway, Garage Door Opener, Guest, Other, Parking Pad, Rv Access/parking, Garage Faces Rear, Golf Cart Parking, Boat
- Sewer:
- Public Sewer
- Utilities Available:
- Cable Available, Natural Gas Available, Underground Utilities, Other, Phone Available, Natural Gas Connected, Sewer Connected, Sprinkler Recycled, Water Connected, Public
- Water Source:
- Public
- Minimum Lease Term:
- 7 Months
- Pets Allowed?
- Subdivision Name:
- MAITLAND PARK SOUTH
- Community Features:
- Street Lights
- Senior Community:
- No
- Listing Terms Considered by Seller:
- Cash, Conventional, FHA, VA Loan
- Occupant Type:
- Vacant
- Lease Considered:
- Yes
- Tax Legal Description:
- MAITLAND PARK SOUTH 1/46 LOT 16
- Real Estate Folio Number (Parcel Number):
- 36-21-29-5473-00-160
- Zoning:
- RSF-2
- Title to the property is held by owner as:
- Fee Simple
- Elementary School:
- Lake George Elem
- High School:
- Winter Park High
- Middle Or Junior School:
- Maitland Middle
- Originally published on:
- November 21, 2025 11:12 am
- Active on the market since:
- November 21, 2025
- Listing Agreement executed on:
- November 19, 2025
- Price change occurred on:
- March 18, 2026 9:30 pm
- Listing Status Last Changed On:
- November 21, 2025 11:12 am
- Photos updated on:
- April 15, 2026 3:07 am
- Last Modified:
- April 15, 2026 3:07 am
- Courtesy of:
- STRICKLAND REALTY GROUP INC
- Attribution:
- 407-448-5068
- Road Surface Type:
- Paved, Asphalt
- Street Name:
- SUNNYSIDE
- Street Number:
- 1421
- City:
- MAITLAND
- State:
- Florida
- Zip Code:
- 32751
- County:
- Orange
- Latitude:
- N28° 36' 55.8''
- Longitude:
- W82° 38' 18''
Neighborhood Stats
Source: U.S. Census Bureau, ACS 5-Year Estimates
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