$1,300,000

1421 SUNNYSIDE DRIVE, MAITLAND

4

Beds

2.5

Baths

2,116 ft2

Property Size

O6358123

MLS #

About The Property

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.

Listing updated: November 22, 2025 at 07:05pm

Listed by Realtor: Amanda Binns

Listed by office:  STRICKLAND REALTY GROUP INC

Source: Stellar MLS

Property Details

Listing Id: O6358123
Price: $1,300,000
Property Size: 2,116 ft2
Property Lot Size: 0 ft2
Rooms: 8
Bedrooms: 4
Bathrooms: 2.5
Architectural Style: Custom, Florida, Other, Patio, Ranch
Bathrooms Full: 2
Bathrooms Half: 1
Modification Timestamp: November 22, 2025 at 08:20pm
Building Area Total: 3030
Construction Materials: Block, Concrete, Other
Cooling: Central Air
CoveredSpaces: 2
CumulativeDaysOnMarket: 1
DaysOnMarket: 1
DirectionFaces: East
ElementarySchool: Dommerich Elem
Fencing: Vinyl
FireplaceFeatures: Living Room
Flooring: Carpet, Ceramic Tile, Terrazzo, Hardwood
FoundationDetails: Slab
Furnished: Unfurnished
GarageSpaces: 2
HighSchool: Winter Park High
Laundry Features: Laundry Room
Levels: One
List AOR: Orlando Regional
List Agent AOR: Orlando Regional
List Agent Email: amandasellsfl@gmail.com
List Agent Full Name: Amanda Binns
List Agent MlsId: 261209628
ListOfficeMlsId: 261010688
List Office Name: STRICKLAND REALTY GROUP INC
ListOfficePhone: 407-448-5068
Listing Terms: Cash, Conventional, FHA, VA Loan
Living Area Source: Public Records
Lot Features: Corner Lot
LotSizeArea: 13422
LotSizeSquareFeet: 13422
MLS Area Major: 32751 - Maitland / Eatonville
MiddleOrJuniorSchool: Maitland Middle
MlsStatus: Active
ModificationTimestamp: November 22, 2025 at 07:05pm
OnMarketDate: 2025-11-21
Originating System Name: Stellar MLS
Ownership: Fee Simple
Parcel Number: 362129547300160
Parking Features: Boat, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Guest, Other, Parking Pad, RV Parking
Pets Allowed: Yes
Pool Features: Child Safety Fence, Heated, In Ground, Lighting, Salt Water, Screen Enclosure
Roof: Shingle
Sewer: Public Sewer
Spa Features: Heated, In Ground
State Or Province: FL
Status Change Timestamp: November 21, 2025 at 11:12am
Stories Total: 1
Street Name: SUNNYSIDE
Street Number: 1421
Street Number Numeric: 1421
Street Suffix: DRIVE
Tax Annual Amount: 5513.32
Tax Block: 00
Tax Book Number: 1-46
Tax Year: 2024
Utilities: Cable Available, Natural Gas Available, Natural Gas Connected, Other, Phone Available, Public, Sewer Connected, Sprinkler Recycled, Street Lights, Underground Utilities, Water Connected
View: Garden, Pool
Water Source: Public
Year Built: 1966
Zoning: RSF-2
FeedTypes: IDX
Source System Key: 774313288
OriginalEntryTimestamp: November 21, 2025 at 11:12am
OriginalListPrice: 1300000

Amenities and Features

Outdoor Details
Garage Attached
Other Features
Dishwasher
Disposal
Eating Space In Kitchen
Electric Water Heater
French Doors
Has a View
Has Cooling System
Has Fireplace
Has Garage
Has Heating System
Has Pool
Irrigation System
Kitchen/Family Room Combo
Lighting
Living Room/Dining Room Combo
Open Floorplan
Open Parking
Other
Primary Bedroom Main Floor
PrimaryBedroom Upstairs
Private Entrance
Private Mailbox
Private Yard
Rain Gutters
Sidewalk
Solid Surface Counters
Solid Wood Cabinets
Storage
Thermostat
Window Treatments

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$6,665.36
per month
  • Principal and Interest
  • Property Tax
  • HOA fee
  • Private Mortgage Insurance
$ 5,040.36

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Disclaimer

Property ID - | 798312

All listings featuring of Stellar MLS are provided by Stellar MLS. This information is not verified for authenticity or accuracy and is not guaranteed. 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 MLS.

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