1421 SUNNYSIDE DRIVE Maitland, FL $ 1,300,000
1421 SUNNYSIDE DRIVE
$ 1,300,000
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1421 SUNNYSIDE DRIVE

Maitland, FL, 32751
$ 1,300,000
Bedrooms4 Baths2.1 Sq 2,116

Monthly Estimate*

$ 8,110

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Single Family Home for sale in Maitland, FL

for $1,300,000 with 4 bedrooms and 2 full baths, 1 half bath. This 2,116 square foot home was built in 1966 on a lot size of 0.31.

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.

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Single Family Active

Price

$ 1,300,000

Bedrooms

4

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 5,513

Style

Custom,Florida,,Patio,Ranch

Lot Size

0.31

Year Built

1966

Town/City

Maitland

County/Region

Orange

MLS | Web ID

O6358123

Features
Interior
Interior Amenities eating space 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 ther
Flooring carpet ceramic tile terrazzo hardwood
Furnished Y/N unfurnished
Fireplace Features living room
Total Stories 1
Air Conditioning Y/N yes
Heating Y/N yes
Fireplace Y/N yes
Half Baths 1
Laundry Features laundry room
Total Bedrooms 4
Total Baths 3
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General
Sewer public sewer
Heating electric
Cooling central air
Utilities cable available natural gas available natural gas connected other phone available public sewer connected sprinkler recycled street lights underground utilities water connected
Roof shingle
Appliances dishwasher disposal electric water heater
Zoning rsf-2
Garage Spaces 2
Patio/Porch Features covered enclosed front porch other patio porch rear porch screened side porch
Architectural Style custom florida other patio ranch
Pool Features child safety fence heated in ground lighting salt water screen enclosure
Construction Materials block concrete other
Pets Allowed yes
Year Built 1966
View garden pool
Levels one
Property Subtype single family residence
Tax Year 2024
Ownership fee simple
County orange
New Construction no
Property Type residential
HOA N
Attached Garage yes
Subdivision Name maitland park south
Facing Direction east
Garage Y/N yes
Total Rooms 8
Full Baths 2
Status active
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 t
High School winter park high
City maitland
Senior Community Y/N no
MLS Area 32751 - maitland / eatonville
Lot Size Units square feet
Lot Size Square Feet 13422
Carport Y/N no
Listing Terms cash conventional fha va loan
Spa Features heated in ground
Elementary School dommerich elem
Land Lease Y/N no
Tax Annual Amount 5513.32
Middle/Junior High School maitland middle
Additional Parcels Y/N no
Lease Considered Y/N yes
Virtual Tour https://www.zillow.com/view-imx/73451cff-1c10-448e-9954-6946e678ec27?wl=true&setattribution=mls&initialviewtype=pano https://www.zillow.com/view-imx/73451cff-1c10-448e-9954-6946e678ec27?wl=true&setattribution=mls&initialviewtype=pano
Building Area Units square feet
Living Area Units square feet
Standard Status active
Occupancy Type vacant
Tax Lot 16
Legal Description maitland park south 1/46 lot 16
Minimum Lease 7 months
Water Access Y/N no
Water View Y/N no
Flood Zone Code x
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Exterior
Exterior Amenities french doors irrigation system lighting other private entrance private mailbox private yard rain gutters sidewalk storage
Vegetation mature landscaping oak trees trees/landscaped
Fencing vinyl
Parking Features boat driveway garage door opener garage faces rear golf cart parking guest other parking pad rv parking
Lot Features corner lot
Water Source public
Lot Size Area 13422
Foundation Details slab
Building Area Total 3030
Lot Size Acres 0.31
Road Surface Type asphalt paved
Private Pool yes
Waterfront Y/N no
Covered Spaces 2
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Internal Only
Street Number 1 1421
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* Excluded Features
List By
Strickland Realty Group Inc

Broker

amandasellsfl@gmail.com

Email

Affordability Calculator

$8,570
Per Month
95%
5%
0%
Monthly Principal & Interest
$8,110
Monthly Property Taxes
$459
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3324815 Elementary School
3324915 Middle School
Winter Park High High School
Pricing History
DatePricePrice ChangeDescription
11/21/2025$1,300,000 Listed Price

Map


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1421 SUNNYSIDE DRIVE, Maitland, FL, 32751 is a Single Family Home for sale at $1,300,000 with 2,116 sqft and a lot size of 0.31. 1421 SUNNYSIDE DRIVE has 4 bedrooms, 2.1 baths, and was built in 1966. The property's zip code is 32751 which is in Maitland, FL