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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.
| DAYS ON MARKET | 121 | LAST UPDATED | 3/18/2026 |
|---|---|---|---|
| TRACT | MAITLAND PARK SOUTH | YEAR BUILT | 1966 |
| COMMUNITY | 32751 - Maitland / Eatonville | GARAGE SPACES | 2.0 |
| COUNTY | Orange | STATUS | Active |
| PROPERTY TYPE(S) | Single Family |
| Elementary School | Dommerich Elem |
|---|---|
| Jr. High School | Maitland Middle |
| High School | Winter Park High |
| PRICE HISTORY | |
| Prior to Feb 5, '26 | $1,300,000 |
|---|---|
| Feb 5, '26 - Feb 20, '26 | $1,224,999 |
| Feb 20, '26 - Mar 18, '26 | $1,199,999 |
| Mar 18, '26 - Today | $1,100,000 |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Dishwasher, Disposal, Electric Water Heater |
| AREA | 32751 - Maitland / Eatonville |
| CONSTRUCTION | Block, Concrete, Other |
| EXTERIOR | Lighting, Other, Private Entrance, Private Yard, Rain Gutters, Storage |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Electric |
| INTERIOR | Eat-in Kitchen, Open Floorplan, Other |
| LOT | 0.31 acre(s) |
| LOT DESCRIPTION | Corner Lot |
| PARKING | Boat, Driveway, Garage Door Opener, Garage Faces Rear, Guest, Other, Parking Pad, RV Access/Parking, Attached |
| POOL | Yes |
| POOL DESCRIPTION | Heated, In Ground, Salt Water, Screen Enclosure, Private |
| SEWER | Public Sewer |
| STORIES | 1 |
| STYLE | Custom, Florida, Other, Patio Home, Ranch |
| SUBDIVISION | MAITLAND PARK SOUTH |
| TAXES | 5513.32 |
| UTILITIES | Natural Gas Available, Cable Available, Natural Gas Connected, Other, Phone Available, Sewer Connected, Underground Utilities, Water Connected |
| VIEW | Yes |
| VIEW DESCRIPTION | Garden, Pool |
| WATER | Public |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listing provided by Amanda Binns, STRICKLAND REALTY GROUP INC, 407-448-5068
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 3/19/26 7:17 PM PDT.
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