$1,300,000
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1421 Sunnyside Drive, Maitland, FL 32751

4 Beds
3 Baths
2,116 Sq Ft
Sat, 11/22
12 PM - 2 PM

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 chefs 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 hallwayfinished in classic terrazzoare 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 upgradesmaking it an exceptional opportunity for anyone looking for a well-maintained, thoughtfully designed property in a prime Central Florida location.

  • MLS# O6358123
  • Date Listed11/19/2025
  • Days on Realty 2 Days
  • Bedrooms 4
  • Bathrooms 2 Full baths, 1 Half baths
  • Lot Size 0.31 acres (13,422 sq. ft)
  • Sewer Public Sewer
  • Subdivision MAITLAND PARK SOUTH
  • Property Type Single Family
  • County Orange
  • Year Built 1966
  • Water Public
  • Square Feet 2,116 sq. ft
  • Price Per Sq. Ft $614.37

Interior Features

  • Appliances Dishwasher, Disposal, Electric Water Heater
  • Flooring Carpet, Ceramic Tile, Terrazzo, Wood
  • Cooling Central Air
  • Heating Electric

Exterior / Lot Features

  • Exterior Lighting, Other, Private Entrance, Private Yard, Rain Gutters, Storage
  • Roof Shingle
  • Lot Size Acres 0.31
  • Lot Size SQFT 13,422.00
  • Lot Features Corner Lot

Financial Considerations

  • Tax Amount $5,513
  • Terms Cash, Conventional, FHA, VA Loan

Nearby Schools

Source: School Digger

Sales & Tax History

Source: Public Records

Population & Environment

Source: Sperling's Best Places

Walkability in FL / 32751

Source: Walkscore

53/100

Somewhat Walkable

Walk Score ®

55/100

Bikable

Bike Score ®

Overview

Some errands can be accomplished on foot. It is possible to get on a bus. Some bike infrastructure.

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 39/100, Transit Score: 16/100, Bike Score: 50/100.

Property Change History

Property description updated with new details

Points of Interest near 1421 SUNNYSIDE DRIVE, MAITLAND, FL 32751

Frequently Asked Questions for 1421 SUNNYSIDE DRIVE

Source: Realty.com

1421 SUNNYSIDE DRIVE, MAITLAND, FL 32751 is a Single Family 2,116 sq. ft. home listed for sale. Realty.com has 55 photos available of this 4 bed, 3 bath house, listed at $1,300,000. View sales and tax history, use our mortgage calculator and more on Realty.com

Realty.com has 55 photos of 1421 SUNNYSIDE DRIVE.

Our records indicate that 1421 SUNNYSIDE DRIVE was built in 1966.

The full address for this home is 1421 SUNNYSIDE DRIVE, MAITLAND, FL 32751.

1421 SUNNYSIDE DRIVE has been listed on Realty.com since Wed November 19, 2025

Some errands can be accomplished on foot. It is possible to get on a bus. Some bike infrastructure.

The average walkability score in the surrounding area is Walk Score: 39/100, Transit Score: 16/100, Bike Score: 50/100.

There are 3 schools assigned to this home. Check out the schools near 1421 SUNNYSIDE DRIVE. Hungerford Elementary School (Grades: PK - 5), Maitland Middle School (Grades: 6 - 8), Winter Park High School (Grades: 9 - 12)

Listing provided courtesy of: STRICKLAND REALTY GROUP INC (tel: 4074485068)
Listing agent: Amanda Binns (#261209628)

This content last refreshed on 2025-11-21 19:06:53. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

Export listing data of 1421 SUNNYSIDE DRIVE, MAITLAND, FL 32751 : MLS# O6358123