1421 SUNNYSIDE, MAITLAND, FL 32751

$1,300,000

Beds: 4

Baths: 2 Full / 1 Half

Sq. Ft.: 2,116 Sq. Ft.

Year Built: 1966

Lot Size: 0.31 Acres

Garage: 2

Pool: Yes

DOM: 1

Property Overview

Status: Active

Property Type: Residential

MLS #: ac25def49e6818c5c5ef606fdbf9a1de

Subdivision: MAITLAND PARK SOUTH

County: Orange

HOA Fee: N/A

Year Built: 1966

Construction: Block, Concrete, Other

Foundation: Slab

Roof: Shingle

Cooling: Central Air

Heating: Electric

Sewer: Public Sewer

Water Source: Public

Zoning: RSF-2

Tax Amount: $5,513.32 (2024)

Listed On: Nov 19, 2025

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.

Exterior Features

French Doors, Irrigation System, Lighting, Other, Private Entrance, Private Mailbox, Private Yard, Rain Gutters, Sidewalk, Storage

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.

School Information

Elementary: Dommerich Elem

Middle: Maitland Middle

High: Winter Park High

Location

Get Directions View on Google Maps

Mortgage Estimator

*Estimate includes Principal & Interest (P&I) only. It does not include taxes, insurance, HOA fees, or PMI. Rates and payments may vary. Consult a lender for accurate figures.

Listing Information

Provided Courtesy of:

STRICKLAND REALTY GROUP INC

Listing Agent: Amanda Binns

Information is deemed reliable but not guaranteed. Information 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.

Data last updated: January 11, 2026, 7:31 am UTC

MLS Source: Stellar MLS Copyright © 2026

Similar Active Listings Nearby

Similar Recently Sold Listings Nearby