1421 SUNNYSIDE DRIVE Maitland, FL $ 1,100,000
1421 SUNNYSIDE DRIVE
$ 1,100,000
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1421 SUNNYSIDE DRIVE

Maitland, FL, 32751
$ 1,100,000
Bedrooms4 Baths2.1 Sq 2,116

Monthly Estimate*

$ 6,773

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View a Virtual Tour

Single Family Home for sale in Maitland, FL

for $1,100,000 with 4 bedrooms and 2 full baths, 1 half bath. This 2,116 square foot home was built in 1966 on a lot size of 0.31.

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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Single Family Active

Price

$ 1,100,000

Bedrooms

4

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 5,513

Style

Custom Florida Other Patio Ranch

Lot Size

0.31

Year Built

1966

Town/City

Maitland

County/Region

Orange

MLS | Web ID

O6358123

Features
General
Sewer Public Sewer
Heating Electric
Cooling Central Air
Utilities Cable Available Natural Gas Available Natural Gas Connected Other Phone Available Public Sewer Connected Sprinkler Recycled Street Lights Underground Utilities Water Connected
Roof Shingle
Appliances Dishwasher Disposal Electric Water Heater
Zoning RSF-2
Garage Spaces 2
Patio/Porch Features Covered Enclosed Front Porch Other Patio Porch Rear Porch Screened Side Porch
Architectural Style Custom Florida Other Patio Ranch
Pool Features Child Safety Fence Heated In Ground Lighting Salt Water Screen Enclosure
Construction Materials Block Concrete Other
Pets Allowed Yes
Year Built 1966
View Garden Pool
Levels One
Property Subtype Single Family Residence
Tax Year 2024
Ownership Fee Simple
County Orange
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name MAITLAND PARK SOUTH
Facing Direction East
Garage Y/N true
Total Rooms 8
Full Baths 2
Status Active
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.
High School Winter Park High
City MAITLAND
Senior Community Y/N false
MLS Area 32751 - Maitland / Eatonville
Lot Size Units Square Feet
Lot Size Square Feet 13422
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Spa Features Heated In Ground
Elementary School Dommerich Elem
Land Lease Y/N false
Tax Annual Amount 5513.32
Middle/Junior High School Maitland Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.zillow.com/view-imx/73451cff-1c10-448e-9954-6946e678ec27?wl=true&setAttribution=mls&initialViewType=pano https://www.zillow.com/view-imx/73451cff-1c10-448e-9954-6946e678ec27?wl=true&setAttribution=mls&initialViewType=pano
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Vacant
Tax Lot 16
Legal Description MAITLAND PARK SOUTH 1/46 LOT 16
Minimum Lease 7 Months
Water Access Y/N false
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Eating Space In Kitchen Kitchen/Family Room Combo Living Room/Dining Room Combo Open Floorplan Other Primary Bedroom Main Floor PrimaryBedroom Upstairs Solid Surface Counters Solid Wood Cabinets Thermostat Window Treatments
Flooring Carpet Ceramic Tile Terrazzo Hardwood
Furnished Y/N Unfurnished
Fireplace Features Living Room
Total Stories 1
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 1
Laundry Features Laundry Room
Total Bedrooms 4
Total Baths 3
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Exterior
Exterior Amenities French Doors Irrigation System Lighting Other Private Entrance Private Mailbox Private Yard Rain Gutters Sidewalk Storage
Vegetation Mature Landscaping Oak Trees Trees/Landscaped
Fencing Vinyl
Parking Features Boat Driveway Garage Door Opener Garage Faces Rear Golf Cart Parking Guest Other Parking Pad RV Parking
Lot Features Corner Lot
Water Source Public
Lot Size Area 13422
Foundation Details Slab
Building Area Total 3030
Lot Size Acres 0.31
Road Surface Type Asphalt Paved
Private Pool true
Waterfront Y/N false
Covered Spaces 2
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* Excluded Features
List By
Strickland Realty Group Inc

Broker

amandasellsfl@gmail.com

Email

Affordability Calculator

$7,232
Per Month
94%
6%
0%
Monthly Principal & Interest
$6,773
Monthly Property Taxes
$459
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Winter Park High High School High School
Pricing History
DatePricePrice ChangeDescription
3/18/2026$1,100,000 -8.33% Price Down
2/20/2026$1,199,999 -2.04% Price Down
2/5/2026$1,224,999 -5.77% Price Down
12/19/2025$1,300,000 Listed Price

Map


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1421 SUNNYSIDE DRIVE, Maitland, FL, 32751 is a Single Family Home for sale at $1,100,000 with 2,116 sqft and a lot size of 0.31. 1421 SUNNYSIDE DRIVE has 4 bedrooms, 2.1 baths, and was built in 1966. The property's zip code is 32751 which is in Maitland, FL