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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.
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.
Property Details
Price:
$999,999
MLS #:
O6358123
Status:
Active
Beds:
4
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
MAITLAND PARK SOUTH
Neighborhood:
32751maitlandeatonville
Listed Date:
Nov 21, 2025
Finished Sq Ft:
2,116
Total Sq Ft:
3,030
Lot Size:
13,422 sqft / 0.31 acres (approx)
Year Built:
1966
See this Listing
Schools
Elementary School:
Dommerich Elem
Middle School:
Maitland Middle
High School:
Winter Park High
Interior
Appliances
Dishwasher, Disposal, Electric Water Heater
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Ceramic Tile, Terrazzo, Hardwood
Heating
Electric
Interior Features
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, Thermostat, Window Treatments
Laundry Features
Laundry Room
Levels
One
Exterior
Architectural Style
Custom, Florida, Other, Patio, Ranch
Attached Garage YN
1
Construction Materials
Block, Concrete, Other
Covered Spaces
2
Direction Faces
East
Exterior Features
French Doors, Irrigation System, Lighting, Other, Private Entrance, Private Mailbox, Private Yard, Rain Gutters, Sidewalk, Storage
Fencing
Vinyl
Garage Spaces
2
Lot Features
Corner Lot
Open Parking YN
1
Parking Features
Boat, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Guest, Other, Parking Pad, RV Parking
Patio And Porch Features
Covered, Enclosed, Front Porch, Other, Patio, Porch, Rear Porch, Screened, Side Porch
Roof
Shingle
Spa Features
Heated, In Ground
View
Garden, Pool
Financial
Tax Year
2024
Taxes
$5,513
Map
Community
- Address1421 SUNNYSIDE DRIVE MAITLAND FL
- SubdivisionMAITLAND PARK SOUTH
- CityMAITLAND
- CountyOrange
- Zip Code32751
Subdivisions in MAITLAND
- ACREAGE & UNREC
- ADAMS GROVE
- BEG 635 FT E & 430 FT N OF SW COR OF SW1/4 OF NE1/
- BRANCH TREE
- BRITTANY GARDENS
- BUCHER HGTS
- CALHOUNS SUB
- CARRINGTON PARK A CONDO
- CHERRYWOOD GARDENS
- COFFINS SUB
- COMMONS AT MAITLAND CENTER SEC 02
- COOL-MORE SUB
- COOPERS SUB
- DIXIE TERRACE
- DOMMERICH
- DOMMERICH ESTATES 1ST ADD
- DOMMERICH ESTATES 2ND ADD
- DOMMERICH HILLS 2ND ADD
- DOMMERICH HILLS 3RD ADD
- DOMMERICH HILLS FIFTH ADD
- DOMMERICH HILLS SECOND ADD
- DOMMERICH WOODS
- DRUID HILLS
- DRUID HILLS PARK
- EATONVILLE
- ENCLAVE/MAITLAND A-F
- ENGLISH ESTATES UNIT 1
- ENGLISH ESTATES UNIT 2
- ENGLISH ESTATES UNIT 3
- ENGLISH ESTATES UNIT 4
- ENGLISH ESTS UNIT 1
- ENGLISH WOODS
- FOREST BROOK
- FOREST BROOK 3RD SEC
- FOREST BROOK 5TH SEC
- GREENWOOD GARDENS REP
- GREENWOOD GARDENS SEC 01
- HAMLET AT MAITLAND
- HIGHLAND PARK ESTATES FIRST ADD
- HOLDEN BROS SUB
- HOLLIEANNA SHORES
- HOLLIEANNA SHORES 1ST ADD
- INDIAN HILLS UNIT 1 REP
- INDIAN HILLS UNIT 9
- KINGS ROW
- LAKE EULALIA HEIGHTS
- LAKE FAITH VILLAS CONDO
- LAKE MAITLAND OWL PRESERVE
- LAKE MAITLAND TERRACE APTS
- LAKE SYBELIA COVE
- LAKEWOOD SHORES 1ST ADD
- MAITLAND CLUB
- MAITLAND EXCHANGE
- MAITLAND GROVE
- MAITLAND HARBOUR APTS
- MAITLAND VILLAGE
- MAITLAND WOODS
- MOORINGS ON LAKE MAITLAND CONDO
- MOORINGS ON LAKE MAITLAND CONDO BLDG 03
- MOORINGS ON LAKE MAITLAND CONDO BLDG 05
- NORTHGATE
- NORTHWOOD HEIGHTS
- OAKLAND SHORES
- OAKLAND SHORES 1ST ADD
- OAKLAND SHORES 3RD ADD REP
- OAKLEIGH 3RD ADD
- OAKWOOD
- ORANGEDALE PARK
- PACKWOODS PLAN/MAITLAND
- PARK LAKE GROVE CONDO PH B
- PARK LAKE SHORES
- PARK LAKE TOWNHOUSES
- PARK LAKE TWNHS
- PARK LAKE TWNHS PH 02
- PARK LAKE VILLAS CONDO
- PARK LAKE VILLAS CONDO CB 2/52
- PARK LAKE WOODS CONDO
- PRESERVE AT MAITLAND
- REPLAT BLK B POORS ADD
- RIDGEWOOD VILLAS CONDO
- ROOSEVELT PLACE
- SHOPPES/MAITLAND
- SIERRA CONDOMINIUMS
- STONEWOOD
- SUN BAY CLUB CONDO
- THOMPSON SUB
- ULTRA VISTA CONDO
- VERSAILLES
- VISCONTI EAST
- VISCONTI EST
- VISCONTI WEST
- VISCONTI WEST BLDG 3
- VISCONTI WEST BLDG 5
- VISCONTI WEST CONDO
- WEST COVE
- WINFIELD
- WOODBRIDGE
Market Summary
Current real estate data for Single Family in MAITLAND as of Apr 29, 2026
84
Single Family Listed
82
Avg DOM
364
Avg $ / SqFt
$1,122,442
Avg List Price
Property Summary
- Located in the MAITLAND PARK SOUTH subdivision, 1421 SUNNYSIDE DRIVE MAITLAND FL is a Single Family for sale in MAITLAND, FL, 32751. It is listed for $999,999 and features 4 beds, 3 baths, and has approximately 2,116 square feet of living space, and was originally constructed in 1966. The current price per square foot is $473. The average price per square foot for Single Family listings in MAITLAND is $364. The average listing price for Single Family in MAITLAND is $1,122,442. To schedule a showing of MLS#o6358123 at 1421 SUNNYSIDE DRIVE in MAITLAND, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.
Similar Listings Nearby
Courtesy of STRICKLAND REALTY GROUP INC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than Charles Rutenberg Realty include the name of the listing broker. Neither the listing company nor Charles Rutenberg Realty shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 1421 SUNNYSIDE DRIVE
MAITLAND, FL

