Date
Details
Price
Change
Source
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.
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1/55
$1,300,000
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Property Description
Welcome to 1421 Sunnyside Drive in Maitland, a beautifully maintained home where timeless design meets modern luxury. This 4-bedroom, 2.5-bath corner lot residence with a pool has a thoughtfully designed indoor and outdoor living space. Its location provides quick access to top-rated schools, boutique shopping, and local dining in one of the most desirable neighborhoods in the Maitland and Winter Park area. From the moment you arrive, the manicured landscaping and inviting covered front porch set the tone. Inside, natural light fills the home through skylights and bay windows, highlighting gleaming hardwood floors and a stunning wood-burning fireplace. The open layout connects each living space seamlessly, creating an ideal flow for everyday living and entertaining. The chef's kitchen serves as the heart of the home, complete with custom hardwood cabinetry, granite countertops, stainless steel appliances, a wine chiller, and a spacious breakfast island with ample seating. Every detail balances style and function, making this kitchen a standout feature. The primary suite offers a peaceful retreat with wood floors and French doors leading directly to the porch. The ensuite bathroom features an oversized shower with spa-style jets and customized storage. Down the hallway-finished in classic terrazzo-are three additional bedrooms and a full bath with custom upgrades. The dining area captures beautiful morning light through the bay window, while a cozy living room with French doors opens to the outdoor living space. The private backyard oasis is designed for year-round enjoyment, featuring a heated pool enclosed by a full screened deck and patio area. Start your day with a sunrise on the front porch and end it with sunset views by the pool, giving the home a seamless indoor-outdoor feel that you will love. Additional highlights include a custom built-in home office with abundant storage, a freshly refinished two-car garage, and an oversized driveway equipped 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. This move-in-ready Maitland home seamlessly combines original charm with modern upgrades-making it an exceptional opportunity for anyone looking for a well-maintained, thoughtfully designed property in a prime Central Florida location.
Full Property Details
Full Property Details for 1421 Sunnyside Dr
General
- Price: $1,300,000
- Taxes: $5,513 (2024)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6358123
- Updated: 11/21/2025
- Added to Site: 57 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 Mailbox, 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
- 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
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Listing agent
— 1421 Sunnyside Dr —
Strickland Realty Group Inc
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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 |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1421 Sunnyside Dr
Tax History
Tax History for 1421 Sunnyside Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$5,513
—
$388,750
3%
2024
$5,513
4%
$377,794
3%
2023
$5,287
8%
$366,790
6%
2021
$4,892
-1%
$345,735
-3%
2022
$4,954
1%
$356,107
4%
2021
$4,892
1%
$340,962
2%
2019
$4,826
1%
$333,296
2%
2018
$4,796
13%
$327,081
12%
2017
$4,248
1%
$290,971
2%
2016
$4,202
-2%
$284,986
1%
2015
$4,282
67%
$283,005
55%
2014
$2,559
4%
$182,643
1%
2013
$2,472
—
$179,944
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 1421 Sunnyside Dr
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1421 Sunnyside Drive, Maitland, FL 32751 (MLS# O6358123) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 1421 Sunnyside Drive is currently listed for $1,300,000 and was received on November 21, 2025. 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.