This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/1
$975,000
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/1
Property Description
One or more photo(s) has been virtually staged. 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.
Full Property Details
Full Property Details for 1421 Sunnyside Dr
General
- Sold For: $975,000
- Taxes: $5,513 (2024)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6358123
- Added to Site: 206 day(s) ago
Rental Information
- Min. Lease: 7 Months
Interior
- Number of Rooms: 8
- Interior Features: Eating Space In Kitchen, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, Other, Primary Bedroom Main Floor, PrimaryBedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Window Treatments
- Fireplace: Yes
- Fireplace(s): Living Room
- Appliances: Dishwasher, Disposal, Electric Water Heater
- Furnishings: Unfurnished
- Flooring: Carpet, Ceramic Tile, Terrazzo, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Laundry Room
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Child Safety Fence, Heated, In Ground, Lighting, Salt Water, Screen Enclosure
- Spa Description: Heated, In Ground
Exterior
- Exterior Features: French Doors, Irrigation System, Lighting, Other, Private Entrance, Private Mailbox, Private Yard, Rain Gutters, Sidewalk, Storage
- Deck/Patio: Covered, Enclosed, Front Porch, Other, Patio, Porch, Rear Porch, Screened, Side Porch
- Porch/Patio/Deck: Covered, Enclosed, Front Porch, Other, Patio, Porch, Rea
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Boat, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Guest, Other, Parking Pad, RV Parking
Location
- Area: 32751 - Maitland / Eatonville
- County: Orange
- Development Name: 32751 - Maitland / Eatonville
- Subdivision: MAITLAND PARK SOUTH
- 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.
- Direction Faces: East
School Information
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park High
Community
- Community Name: 32751 - Maitland / Eatonville
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable TV Available, Natural Gas Available, Natural Gas Connected, Other, Phone Available, Public, Sewer Connected, Sprinkler Recycled, Street Lights, Underground Utilities, Water Connected
Structural Information
- Architectural Info: Custom, Florida, Other, Patio, Ranch
- Architectural Style: Custom, Florida, Other, Patio, Ranch
- Exterior Const.: Block, Concrete, Other
- Roof: Shingle
- Stories/Levels: One
- Square Feet: 2,116
- Sq. Ft. Source: Public Records
- Living Area: 2,116 Sq. Ft.
- Year Built: 1966
Lot Features
- Property View: Garden, Pool
- Lot Size (Acres): 0.31
- Lot Size (Sq. Ft.): 13,422
- Lot Size: 13422
- Street/Road Desc.: Asphalt, Paved
- Fencing (Description): Vinyl
Financial Considerations
- Tax Amount: $5,513.32
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: MAITLAND PARK SOUTH 1/46 LOT 16
- Flood Zone Info: X
- APN: 362129547300160
- Property ID: 362129547300160
Listed by Strickland Realty Group Inc
Sold by Keller Williams Winter Park
Get Pre-Approved Today
Schools
Schools serving 1421 Sunnyside Dr
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Dommerich Elementary School 601 North Thistle Lane, Maitland, FL 32751 | K-5 | 1.6 mi |
Maitland Middle School 701 North Thistle Lane, Maitland, FL 32751 | 6-8 | 1.7 mi |
Winter Park High School 2100 Summerfield Road, Winter Park, FL 32792 | 9-12 | 3.2 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1421 Sunnyside Dr
Date
Details
Price
Change
Source
5/22/2026
Sold
$975,000
-2.5%
MLS
4/24/2026
Price Reduced
$999,999
-9.09%
MLS
3/18/2026
Price Reduced
$1,100,000
-8.33%
MLS
2/20/2026
Price Reduced
$1,199,999
-2.04%
MLS
2/05/2026
Price Reduced
$1,224,999
-5.77%
MLS
11/21/2025
Listed
$1,300,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
1421 Sunnyside Drive, Maitland, FL 32751 (MLS# O6358123) is a Single Family property that was sold at $975,000 on May 22, 2026. Want to learn more about 1421 Sunnyside Drive? Do you have questions about finding other Single Family real estate for sale in Maitland? You can browse all Maitland real estate or contact a Coldwell Banker agent to request more information.

