1421 Sunnyside Dr, Maitland, FL 32751 | For Sale

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For Sale $1,224,999 ($578.92 per Sq Ft)

$1,224,999 ($578.92 per Sq Ft)
  • (0)
  • 4 Bedrooms
  • 3 Bathrooms
  • 2,116 Sq Ft
  • 13,422 Sq Ft

Description

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.

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Amenities

Garage
Pool
Garden
Security System
Internet
Telephone
Heating
Fireplace
Balcony & Patio
TV / Cable
Laundry
Hardwood Floors
Spa
Air Conditioning
Solar Power
Floor Plan
Great Views
Natural Light
Quiet
Water View
Elevator
Guest Unit(s)
Furnished
220 Volt

Income

Rental Units


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Expenses

Property Details

List Price $1,224,999
Property Type Single Family Homes
Usable Sqft 2,116
Number of Stories 1 stories
Parking Spots 2 spots
Year Built 1966
Last Sold Unknown
Sold Price Unknown
APN # 362129547300160
MLS # O6358123
Property ID 317453069
Lot Sqft 13,422
Zoning RSF-2
Days on Market 80
Original List Price $1,300,000
Applicances Dishwasher, Disposal, Electric Water Heater%
Date Updated February 07, 2026
Date Created November 19, 2025
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Listing Provided By

Amanda Binns an agent of .


© 2026 STELLAR MLS. All rights reserved. Some listings on this website are from STELLAR as of February 07, 2026 The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.



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