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Property for sale at 1421 SUNNYSIDE DRIVE, MAITLAND, FL, 32751

1421 Sunnyside DriveMaitland, FL, 32751

4beds
3baths
2,116sqft
Single Family Residence
Built in 1966
$975,000
Sold
Price per sqft
$461
Sold on
May 22, 2026
MLS #O6358123Updated May 23, 2026

About this property

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.

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Property details

Property type
Single Family Residence
Street address
1421 Sunnyside Drive
City
Maitland
State
FL
ZIP code
32751
Year built
1966
New construction
No
Faces
East
Rooms
8
Building stories
1
Living area
2,116 sqft
Total building area
3,030 sqft
Architectural style
Other, Ranch
Levels
One

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at November 8, 2026 at 7:45 AM EST

Price & sale history

EventPrice
SoldMLS #O6358123$975,000
Price reducedMLS #O6358123$999,999Change: −23.1%−$300,001
Listed for saleMLS #O6358123$1,300,000
History may be incomplete.
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Location

Property for sale at 1421 SUNNYSIDE DRIVE, MAITLAND, FL, 32751
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