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1655 Sunnyside Drive

Maitland, FL 32751

3 beds
2 baths
1,418 sqft
7,497 sqft lot
$518 per sqft
1950 build
– on site

Welcome to this one-of-a-kind vintage charmer in the heart of Maitland, Florida! Nestled on a beautifully landscaped corner lot, this 3-bedroom, 2-bathroom historic cottage offers 1,418 square feet of thoughtfully designed living space. Just minutes from downtown Maitland and the vibrant energy of Winter Park, you’ll love the perfect blend of convenience and character this home delivers. Step inside and feel the warmth of a home that truly has soul. The open floor plan flows effortlessly throughout, creating a seamless space that’s perfect for both relaxing and entertaining. The fully updated kitchen is a dream — stylish, functional, and ready for your next dinner party. The master bedroom is a true retreat with soaring vaulted ceilings and serene natural light, while each room in the house tells its own story with vintage touches and inviting charm. Outside, you’ll find a lush, landscaped yard designed for both beauty and privacy. The circle driveway adds curb appeal and ease, and the hot tub out back is ready for those laid-back Florida evenings under the stars. From the moment you arrive, you’ll see — and feel — the love and character that lives here. This isn’t just a house; it’s a home with a heartbeat. Roof: 2021 AC: 2021 Plumbing: Updated 2021 Electrical: Updated 2021

Listing courtesy of STELLAR_MLS / KELLER WILLIAMS WINTER PARK

Last checked: Checking… • Last updated May 17, 2025 •

MLS# O6302769 —

The Building

Year Built:

1950
New Construction:

false
Construction Materials:

Block
Levels:

One
Stories Total:

1
Roof:

Shingle
Foundation Details:

Crawlspace
Building Area Total:

1766
Building Area Units:

Square Feet
Building Area Source:

Public Records

Interior

Interior Features:

Primary Bedroom Main Floor
Flooring:

Ceramic Tile
Fireplace:

false

Room Dimensions

Living Area:

1418
Living Area Units:

Square Feet
Living Area Source:

Public Records

Location

Directions:

Start on I-4 East: If you're coming from downtown Orlando, head north on I-4 East toward Maitland.? Take Exit 90 for FL-414 East/Maitland Blvd: Merge onto FL-414 East/Maitland Blvd via Exit 90.? Continue on Maitland Blvd: Stay on Maitland Blvd for approximately 1.5 miles.? Merge onto US-17/92 North (Orlando Ave): Merge right onto US-17/92 North (Orlando Ave) and continue for about 0.5 miles.? Turn Left onto Sybelia Parkway: Turn left onto Sybelia Parkway just before the Publix Super Market.? Continue to Sunnyside Drive: Follow Sybelia Parkway, and then turn left onto Sunnyside Drive.? Arrive at 1655 Sunnyside Drive: Your destination will be on the right at the corner of Sunnyside Drive and Alpine Drive.
Latitude:

28.613397
Longitude:

-81.361506
Coordinates:

-81.361506, 28.613397

The Property

Parcel Number:

362129211211071
Property Type:

Residential
Property Subtype:

Single Family Residence
Lot Size Acres:

0.17
Lot Size Area:

7497
Lot Size SqFt:

7497
Lot Size Units:

Square Feet
Total Acres:

0 to less than 1/4
Zoning:

RSF-2
Direction Faces:

South
View:

false
Exterior Features:

Irrigation System
Water Source:

Public
Road Surface Type:

Paved
Flood Zone Code:

X
Additional Parcels:

false
Homestead:

false
Lease Restrictions:

false
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Lot:

7
Tax Block:

K
Tax Legal Description:

DIXIE TERRACE UNIT NO 2 N/31 E 75 FT LOTS 7 & 8 BLK K
Tax Book Number:

N-31
Tax Annual Amount:

$9,661.15

Beds

Bedrooms Total:

3

Baths

Total Baths:

2
Total Baths:

2
Full Baths:

2

The Listing

Virtual Tour URL Unbranded:

https://www.propertypanorama.com/instaview/stellar/O6302769
Special Listing Conditions:

None

Heating & Cooling

Heating:

Central
Heating:

true
Cooling:

Central Air
Cooling:

true

Utilities

Utilities:

BB/HS Internet Available
Sewer:

Public Sewer

Appliances

Appliances:

Dishwasher
Laundry Features:

Inside

The Community

Subdivision Name:

DIXIE TERRACE
Senior Community:

false
Waterview:

false
Water Access:

false
Waterfront:

false
Pool Private:

false
Association:

false
Ownership:

Fee Simple

Parking

Garage:

false
Carport:

false

Monthly cost estimate

Asking price

$734,990

Expense	Monthly cost
Mortgage	$3,935
Taxes	$805
Insurance	$202
Utilities	$195 See report
Total	$5,137/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Soundscore™

Provided by HowLoud

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
5/1/25 May 1, 2025	Price Changed	STELLAR_MLS	$734,990	-2.0%
4/24/25 Apr 24, 2025	Listed / Active	STELLAR_MLS	$749,990	7.1% (6.3% / YR)
4/4/25 Apr 4, 2025	Price Changed	STELLAR_MLS

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This house located in Maitland Park South, Maitland, FL 32751 is currently for sale for $734,990. 1655 Sunnyside Drive is a 1,418 square foot house with 3 beds and 2 baths that has been on Estately for 24 days. 1655 Sunnyside Drive is in the Maitland Park South neighborhood of Maitland and has a WalkScore® of 69, making it somewhat walkable. This house is in the attendance area of Maitland Middle School, Cornerstone Charter Academy High School, Winter Park High School, Cornerstone Charter Academy K-8, and Dommerich Elementary School.

Listing Courtesy of: STELLAR_MLS and KELLER WILLIAMS WINTER PARK.

Based on information from the My Florida Regional MLS DBA Stellar MLS 2025.

All information provided is deemed reliable but is not guaranteed and should be independently verified. Stellar MLS, Estately and their affiliates provide the MLS and all content therein “AS IS” and without any warranty, express or implied. The information included in this listing is provided exclusively 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. The information on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. Stellar MLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law. For any questions please call (407) 499-8911.