PerformAction
 logo  logo  logo
  • Sign In / Sign Up
  • 855-242-9926
  • BUYING
    • Search Homes
    • Homes New to Market
    • Open Houses
    • Luxury
      • Royal Elite $1.5M +
      • Royal Collection
    • Lifestyle
      • Waterfront & Gulf‑Access
      • Beachfront Condos
      • Golf Communities
  • SELLING
    • WHAT’S MY HOME WORTH
    • Marketing Plan
    • Royal Elite - Sold Listings
  • COMMUNITIES
    • Naples
    • Captiva Island
    • Sanibel Island
    • Bonita Springs
    • Cape Coral
    • Fort Myers
    • Fort Myers Beach
    • Estero
    • ocala
    • North Carolina
    • Market Statistics
  • ABOUT
    • Our Agents
    • Our Management Team
    • Our Offices
    • Join our Team
    • Luxury Portfolio International
    • Relocation Services
    • Assured Title
    • Newsletter
    • HomeVue Magazine
    • World Equestrian Center Magazine
  • BLOG
  • CONTACT
  • Vacation Rentals
    • BUYING
      • Search Homes
      • Homes New to Market
      • Open Houses
      • Luxury
        • Royal Elite $1.5M +
        • Royal Collection
      • Lifestyle
        • Waterfront & Gulf‑Access
        • Beachfront Condos
        • Golf Communities
    • SELLING
      • WHAT’S MY HOME WORTH
      • Marketing Plan
      • Royal Elite - Sold Listings
    • COMMUNITIES
      • Naples
      • Captiva Island
      • Sanibel Island
      • Bonita Springs
      • Cape Coral
      • Fort Myers
      • Fort Myers Beach
      • Estero
      • ocala
      • North Carolina
      • Market Statistics
    • ABOUT
      • Our Agents
      • Our Management Team
      • Our Offices
      • Join our Team
      • Luxury Portfolio International
      • Relocation Services
      • Assured Title
      • Newsletter
      • HomeVue Magazine
      • World Equestrian Center Magazine
    • BLOG
    • CONTACT
    • Vacation Rentals
Sign In / Sign Up
Clear Price
Cancel
Done Search

1421 SUNNYSIDE DRIVE, Maitland, FL 32751 (Sold on )

  • Open House
  • New Listing
  • Price Reduced$100,001
  • Virtual Open House
  • Pending
  • PENDING UNDER CONTRACT
  • The seller has accepted an offer on this property.
  • Virtual Tour

 $999,999

  • Property Info
  • Photos
  • Print
  • Virtual Tour
  • Floor Plan
  • Saved Save Listing
  • Share Listing
  • Virtual Tour
more_vert
  • Property Info
  • Photos
  • Print
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
gallery
  • 4 BedBeds
  • 3 BathBaths
  • 2,116 SqFtSqFt
  • TypeResidential
  • Active
  • MLS# O6358123

Virtual Tour

VirtualTourImage
VirtualTourImage
VirtualTourImage

Property Description

One or more photo(s) has been virtually staged. Priced below appraised value for a limited opportunity to capture instant equity. 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.

Thank you for requesting a showing of this property. A representative will be in touch with you shortly to confirm the requested showing date and time.
Please note that your appointment is not confirmed until someone contacts you.

Request Info / Schedule Showing

Submit

Property Details 1421 SUNNYSIDE DRIVE, MAITLAND, FL 32751

Facts & Features

  • MLS #: O6358123
  • Status: Active
  • Type: Residential
  • SubType: Single Family Residence
  • Year Built: 1966
  • Price: $999,999
  • Acres: 0.31
  • Area: 32751 - Maitland / Eatonville
  • County: Orange
  • Bedrooms: 4
  • Bathrooms: 3
  • Full Baths: 2
  • Half Baths: 1
  • Total SqFt: 2,116

Amenities

  • Parking: Boat, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Guest, Other, Parking Pad, RV Access/Parking
  • Garage Spaces: 2
  • View: Garden, Pool
  • Waterfront: No
  • Pool: Yes
  • Pool Type: Child Safety Fence, Heated, In Ground, Lighting, Salt Water, Screen Enclosure
  • Spa: Yes
  • Spa Type: Heated, In Ground
  • Pets: Yes

Interior Features

  • Interior Features: Eat-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, Wood
  • Utilities: Cable Available, Natural Gas Available, Natural Gas Connected, Other, Phone Available, Public, Sewer Connected, Sprinkler Recycled, Underground Utilities, Water Connected
  • Heating: Electric
  • Cooling: Central Air
  • # of Stories: 1

Exterior Features

  • Style: Custom, Florida, Other, Patio Home, Ranch
  • Exterior Features: French Doors, Lighting, Other, Private Entrance, Private Mailbox, Private Yard, Rain Gutters, Sidewalk, Storage
  • Lot Description: Corner Lot
  • Roof: Shingle
  • Construction: Block, Concrete, Other

Schools

  • Elementary: Dommerich Elem
  • Middle: Maitland Middle
  • High: Winter Park High

Additional Information

  • List Date: 11/21/2025
  • Zoning: RSF-2

Tax Information

  • Tax Amount: $5,513
  • Tax Year: 2024

Estimated Monthly Mortgage Calculator

This calculator is provided for informational purposes. You should not make any decisions based simply on the information provided. Values indicated are estimates and may not be accurate and are only to be used as a guide. This calculator should not be relied upon in any way as the sole source of information. Please consult your financial, tax or legal advisers for an accurate assessment of your mortgage payments and any advice relating to your personal circumstances.

Output format

 

Similar Listings

    • Open House
    • Price Reduced
    • New Listing
    • Pending
    • Pending Under Contract
    • Coming Soon
    • Virtual Open House
    • Virtual Tour
    • Sold
    • Leased
    51 OAKLEIGH LANE, Maitland
    $1,240,000
    MLS# O6399404Residential
    4,149 Sq. Ft.
    4 BEDS4 BATHS
    Request Info
    Delete
    51 OAKLEIGH LANE, MaitlandDetails
      • Open House
      • Price Reduced$95,000
      • New Listing
      • Pending
      • Pending Under Contract
      • Coming Soon
      • Virtual Open House
      • Virtual Tour
      • Sold
      • Leased
      67 CYPRESS LANE, Maitland
      $1,130,000
      MLS# O6371328Residential
      2,292 Sq. Ft.
      4 BEDS3 BATHS
      Request Info
      Delete
      67 CYPRESS LANE, MaitlandDetails
        • Open House
        • Price Reduced$99,000
        • New Listing
        • Pending
        • Pending Under Contract
        • Coming Soon
        • Virtual Open House
        • Virtual Tour
        • Sold
        • Leased
        791 SEQUOIA TRAIL, Maitland
        $1,100,000
        MLS# O6340919Residential
        4,144 Sq. Ft.
        5 BEDS4 BATHS
        Request Info
        Delete
        791 SEQUOIA TRAIL, MaitlandDetails
          • Open House
          • Price Reduced
          • New Listing
          • Pending
          • Pending Under Contract
          • Coming Soon
          • Virtual Open House
          • Virtual Tour
          • Sold
          • Leased
          1665 KING ARTHUR CIRCLE, Maitland
          $1,100,000
          MLS# O6399064Residential
          3,019 Sq. Ft.
          4 BEDS3 BATHS
          Request Info
          Delete
          1665 KING ARTHUR CIRCLE, MaitlandDetails
            • Open House
            • Price Reduced
            • New Listing
            • Pending
            • Pending Under Contract
            • Coming Soon
            • Virtual Open House
            • Virtual Tour
            • Sold
            • Leased
            987 BRIGHTWATER CIRCLE, Maitland
            $1,100,000
            MLS# O6401747Residential
            3,270 Sq. Ft.
            5 BEDS4 BATHS
            Request Info
            Delete
            987 BRIGHTWATER CIRCLE, MaitlandDetails
              • Open House Sun. May 03; 01:00 PM - 04:00 PM
              • Price Reduced
              • New Listing
              • Pending
              • Pending Under Contract
              • Coming Soon
              • Virtual Open House
              • Virtual Tour
              • Sold
              • Leased
              1001 VERSAILLES COURT, Maitland
              $1,050,000
              MLS# O6401795Residential
              3,625 Sq. Ft.
              4 BEDS3 BATHS
              Request Info
              Delete
              1001 VERSAILLES COURT, MaitlandDetails
                • Open House Sun. May 03; 12:00 AM - 03:00 PM
                • Price Reduced$51,000
                • New Listing
                • Pending
                • Pending Under Contract
                • Coming Soon
                • Virtual Open House
                • Virtual Tour
                • Sold
                • Leased
                921 N THISTLE LANE, Maitland
                $1,049,000
                MLS# R4911080Residential
                2,300 Sq. Ft.
                4 BEDS3 BATHS
                Request Info
                Delete
                921 N THISTLE LANE, MaitlandDetails
                  • Open House
                  • Price Reduced$28,950
                  • New Listing
                  • Pending
                  • Pending Under Contract
                  • Coming Soon
                  • Virtual Open House
                  • Virtual Tour
                  • Sold
                  • Leased
                  1610 LYNDALE BOULEVARD, Maitland
                  $1,021,000
                  MLS# G5109784Residential
                  2,598 Sq. Ft.
                  4 BEDS4 BATHS
                  Request Info
                  Delete
                  1610 LYNDALE BOULEVARD, MaitlandDetails
                    • Open House Sat. May 02; 01:00 PM - 03:00 PM
                    • Price Reduced
                    • New Listing
                    • Pending
                    • Pending Under Contract
                    • Coming Soon
                    • Virtual Open House
                    • Virtual Tour
                    • Sold
                    • Leased
                    755 WOODSIDE ROAD, Maitland
                    $999,999
                    MLS# O6402797Residential
                    3,049 Sq. Ft.
                    3 BEDS3 BATHS
                    Request Info
                    Delete
                    755 WOODSIDE ROAD, MaitlandDetails
                      • Open House Sun. May 03; 12:00 PM - 04:00 PM
                      • Price Reduced
                      • New Listing
                      • Pending
                      • Pending Under Contract
                      • Coming Soon
                      • Virtual Open House
                      • Virtual Tour
                      • Sold
                      • Leased
                      1281 WELLINGTON TERRACE, Maitland
                      $979,000
                      MLS# TB8499961Residential
                      2,931 Sq. Ft.
                      4 BEDS4 BATHS
                      Request Info
                      Delete
                      1281 WELLINGTON TERRACE, MaitlandDetails
                        • Open House
                        • Price Reduced$20,000
                        • New Listing
                        • Pending
                        • Pending Under Contract
                        • Coming Soon
                        • Virtual Open House
                        • Virtual Tour
                        • Sold
                        • Leased
                        790 S LAKE SYBELIA DRIVE, Maitland
                        $975,000
                        MLS# G5108209Residential
                        2,021 Sq. Ft.
                        3 BEDS3 BATHS
                        Request Info
                        Delete
                        790 S LAKE SYBELIA DRIVE, MaitlandDetails
                          • Open House
                          • Price Reduced
                          • New Listing
                          • Pending
                          • Pending Under Contract
                          • Coming Soon
                          • Virtual Open House
                          • Virtual Tour
                          • Sold
                          • Leased
                          1817 BRAELOCH COURT, Maitland
                          $974,900
                          MLS# O6389512Residential
                          2,872 Sq. Ft.
                          4 BEDS3 BATHS
                          Request Info
                          Delete
                          1817 BRAELOCH COURT, MaitlandDetails
                          Bonita Springs Logo

                          SIGN UP FOR FREE

                          Get first-in-line listing updates, save favorites & much more by signing up for free

                          MONTHLY NEWSLETTER

                          Office Address

                          View our office locations

                          Contact

                          Phone: 855-242-9926
                          realestate@royalshellrealestate.com
                          Terms of Use Privacy Policy Accessibility Statement
                          • Comparison List   0