Sarasota's Premier Homes

Custom, Florida, Other, Patio Home, Ranch

1421 SUNNYSIDE DRIVE

MAITLAND , FL 32751

MLS#: O6358123

$1,300,000

Status: Active
Listing number: O6358123
Listing provided by: STRICKLAND REALTY GROUP INC
Listing agent phone: None
Last update: a month ago
On site: a month ago
Browse Properties
MAITLAND PARK SOUTH - Residential

Property

Beds

4

Full Baths

2

1/2 Baths

1

Year Built

1966

Sq.Footage

2,116

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.

Features & Amenities

Interior

  • Other Interior Features

    Eat-in Kitchen, Open Floorplan, Other

  • Total Bedrooms

    4

  • Bathrooms

    2

  • 1/2 Bathrooms

    1

  • Cooling YN

    YES

  • Cooling

    Central Air

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Electric

  • Pet friendly

    Yes

Exterior

  • Garage

    Yes

  • Garage spaces

    2

  • Construction Materials

    Block, Concrete, Other

  • Other Exterior Features

    Lighting, Other, Private Entrance, Private Yard, Rain Gutters, Storage

  • Parking

    Boat, Driveway, Garage Door Opener, Garage Faces Rear, Guest, Other, Parking Pad, RV Access/Parking, Attached

  • Patio and Porch Features

    Covered, Enclosed, Front Porch, Other, Patio, Porch, Rear Porch, Screened, Side Porch

  • Pool

    Yes

  • Pool Features

    Heated, In Ground, Salt Water, Screen Enclosure, Private

  • Waterfront YN

    NO

  • View

    Garden, Pool

Area & Lot

  • Lot Features

    Corner Lot

  • Lot Size(acres)

    0.31

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Custom, Florida, Other, Patio Home, Ranch

Price

  • Sales Price

    $1,300,000

  • Tax Amount

    5513.32

  • Sq. Footage

    2, 116

  • Price/SqFt

    $614

HOA

  • Association

    No

School District

  • Elementary School

    Dommerich Elem

  • Middle School

    Maitland Middle

  • High School

    Winter Park High

Property Features

  • Stories

    1

  • Foundation Details

    Slab

  • Ownership

    Fee Simple

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Tax Lot

    16

  • Water Source

    Public

Schedule a Showing

Showing scheduled successfully.

<
>
IN PERSON
VIA CHAT

What is 3 + 4 ?


Change time

Mortgage calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.

Your payment

Principal and Interest:

$

Property taxes:

$

HOA fees:

$

Total loan payment:

$

Total interest amount:

$

Location

County

Orange

Elementary School

Dommerich Elem

Middle School

Maitland Middle

High School

Winter Park High

Listing Courtesy of Amanda Binns , STRICKLAND REALTY GROUP INC

RealHub Information is provided exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. RealHub website owner shall not be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.

Agent Michael Graf

Business Coach | Executive Sales Associate | Realtor®

Michael Graf

Call Michael today to schedule a private showing.

(941) 315-6980

michael@thegrafgroupvip.com


* Listings on this website come from the FMLS IDX Compilation and may be held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work please click here to review our DMCA policy and learn how to submit a takedown request.© 2024 FMLS.
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.

1421 SUNNYSIDE DRIVE

Message successfully sent.

What would you like to know?

What is 3 + 4 ?

Related Properties

New on site 1 day ago
Nestled in the QUIET, oak tree lined and GATED community of LAKE SYBELIA COVE, this CUSTOM-built TUSCAN-style home offers a respite from the outside world and over 3,000 sq. ft of incredibly beautiful and tranquil living space along with the convenience of daily walks around Lake Sybelia. This IMMACULATE 4-bedroom, 3.5-bath residence features thoughtful design and QUALITY CRAFTSMANSHIP throughout. The GOURMET KITCHEN is equipped with custom cabinetry, granite countertops, an onyx backsplash, a GAS cooktop, and stainless steel appliances, including premium additions like a Viking FRENCH DOOR wall oven, Wolf steam oven, and Bosch dishwasher. On the main floor, the primary suite provides convenience and privacy, along with a second bedroom and full bath. Upstairs, two additional bedrooms each open to private BALCONIES—one offering an impressive VIEW of LAKE SYBELIA. Elegant tray ceilings with crown molding accent the living room, dining room, and primary bedroom. Marble tile flooring flow seamlessly throughout the home, complemented by red oak stairs with wrought iron railings and wide 7.5-inch baseboards. Built for comfort and efficiency, the home includes a RADIANT BARRIER for energy savings, foam-insulated masonry walls on the first floor for better insulation and sound reduction, a whole-house water filtration system, and a GAS water heater. Outdoor spaces include a screened back patio, updated balconies with new drains and flooring, front porch pavers, French drains, and gutters on both the front and back.Recent updates ensure the home is move-in ready. Here are a few of the most recent improvements. NEW tile roof (2023), Exterior painting (2023), Marble flooring installation (2023), Interior painting (2024), Upstairs and downstairs Carrier heat pump HVAC systems (2024 and 2025). Additional enhancements from prior years include CUSTOM front doors and Plantation Shutters on all windows. Located in an excellent school district and just 3 miles from the RDV Sportsplex, this home is conveniently close to the dining, shopping, and all the cultural amenities of MAITLAND and nearby WINTER PARK. Make sure to see the attached video and 3D VIRTUAL Walk Through.
#O6370776

MAITLAND

890 CRANES COURT

4 Beds

3 Baths

3,221 Sq.Ft.

$1,100,000

MLS#: O6370776

Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths. Step inside to discover hardwood floors flowing throughout the first level, leading to a dramatic sunken living room and formal dining room perfect for entertaining. The heart of the home is the spectacular family room featuring soaring 17-foot ceilings, a wood-burning fireplace, and expansive windows that bathe the space in natural light. The well-appointed kitchen boasts granite countertops, a charming breakfast nook, and glass sliders opening to a covered side porch—ideal for morning coffee or evening relaxation. The main level also includes a convenient guest bedroom and full bath, separate living and dining rooms, plus an attached 2-car garage. Upstairs, retreat to the loft-style primary suite with private en suite bath, two additional guest bedrooms, a hall bath, and laundry facilities for ultimate convenience. Outdoor living shines here with a front deck off the family room and multiple porch spaces. The quiet, dead-end street ensures peace and privacy. For just $100/year, the optional HOA provides deeded park access to beautiful Lake Maitland directly across the street—feel the refreshing lake breeze from your front door! Just minutes from the Winter Park Racquet Club and all that downtown Winter Park and Maitland have to offer. Zoned for award-winning Dommerich Elementary, Maitland Middle, and Winter Park High School. Complete with Terminix termite bond for peace of mind. This tranquil neighborhood retreat offers a rare combination of custom quality, natural beauty, and an unbeatable location. Don't miss this exceptional opportunity!
#O6371328

MAITLAND

67 CYPRESS LANE

4 Beds

3 Baths

2,292 Sq.Ft.

$1,339,000

MLS#: O6371328

Built in 2014 and set within the highly sought-after Dommerich Estates neighborhood of Maitland, this thoughtfully maintained two-story home offers a rare blend of space, function, and location. With five bedrooms, three full bathrooms, and a flexible bonus room, the layout is designed to adapt easily to modern living. The entry opens to a formal dining space, while an additional room just off the foyer provides an ideal spot for a home office, den, or reading lounge. Dark hardwood floors anchor the main living areas and create a warm, cohesive feel throughout. At the heart of the home, the open kitchen and family room flow seamlessly together and look out over the backyard—perfect for both relaxed evenings and hosting gatherings. The kitchen features Bosch stainless steel appliances, granite countertops, a generous island with seating, and custom maple cabinetry, offering both style and practicality. The primary suite is privately positioned on the main level and includes two walk-in closets. Its en-suite bath is finished with double vanities, a soaking tub, a separate shower, and ceramic tile throughout. Two additional bedrooms on the first floor share a full bathroom with ceramic tile and a granite-topped vanity. Upstairs, a spacious bonus room creates endless possibilities, accompanied by two more bedrooms connected by a Jack-and-Jill bathroom with matching granite and tile finishes. Notable extras include an interior laundry room with washer and dryer, dual HVAC systems, and a fully fenced backyard with a lovely patio and plenty of room to add a pool or play area. Ideally located just moments from the new boardwalk leading to Maitland Community Park, residents enjoy easy access to walking paths, green space, playgrounds, and nearby tennis courts, enhancing the neighborhood’s active and outdoor lifestyle. Zoned for Dommerich Elementary, Maitland Middle, and Winter Park High School, the home also grants access to Lake Minnehaha, where residents enjoy a private boat ramp and fishing dock. A standout opportunity in one of Maitland’s most established and beloved lakefront communities. This home is back on the market after the previous buyer experienced a personal change in plans. No issues with the property.
#O6369539

MAITLAND

1750 CHEYENNE TRAIL

5 Beds

3 Baths

2,868 Sq.Ft.

$1,200,000

MLS#: O6369539

Price reduced
Discover a rare opportunity in Dommerich Woods, a distinguished and established Maitland neighborhood celebrated for its rich heritage. Situated on .33 acre of lushly landscaped grounds, this remarkable property welcomes with paver drive and enjoys a tranquil setting along a peaceful creek connecting Lake Minnehaha and Lake of the Woods - creating an atmosphere of natural elegance and privacy. Re-roofed in 2023, this expansive 5 bedroom, 3 1/2 bath residence offers 4,144 HSF, and WHOLE HOUSE WATER SOFTNER, showcases a versatile TWO-LEVEL design, perfectly suited for refined living and gracious entertaining. The main level opens with a foyer leading into a bright, open living and dining area, where CEILING FANS throughout the main level add comfort and elegance. From here, step out onto the COVERED UPPER DECK with sweeping views of the SCREENED POOL, TROPICAL GARDEN, and serene backyard retreat - an ideal setting for morning coffee or evening gatherings. At the heart of the home, the GOURMET KITCHEN blends style and functionality with SOLID WOOD CABINETRY, a built-in WINE REFRIGERATOR and WINE RACK, granite countertops, and a CENTER ISLAND with SEATING, and REVERSE OSMOSIS WATER SYSTEM under the DOUBLE SINK. The adjacent laundry room offers exceptional storage, keeping household essentials organized. For added convenience , a two-car garage with built-in cabinets and workshop area, adjoins the spacious laundry room that has granite counters and washer and dryer. Also on the main level , adjacent to the primary bedroom with en-suite bath, a bedroom has been thoughtfully converted into a large closet featuring a CUSTOM CLOSET system, providing abundant space for wardrobe organization. Both levels feature inviting WOOD-BURNING FIREPLACES that add ambiance to the living spaces. On the lower level, a spacious family room, kitchenette, study/library/office, two bedrooms, full bath and half bath provide the perfect complement to easy living. Along the hallway, built-in wood shelving creates a refined showcase for books, art, or personal collections. While one bedroom includes a custom built in desk- ideal for work or study, a second bedroom adds flexibility for creative projects. This level opens onto the screened pool and patio area, designed for seamless indoor-outdoor living. Outside, tropical plantings, METERED IRRIGATION, and a winding private walkway leads along the soft murmur of the BORDERING CREEK. An added bonus is the storage room located below the kitchen which is approximately 375 sq.ft. Whether hosting guests or enjoying a quiet evening, this private oasis offers the ultimate backdrop for relaxed Florida living. Enjoy the opportunity to join the Dommerich Beach Civic Association with membership options including access to a private picnic area, boat ramp, canoe and kayak storage, and unforgettable evening sunsets. With its rare combination of design, flexible spaces, and an idyllic setting , this residence presents a unique opportunity to experience the very best of Maitland and Central Florida living. All this is convenient to some of Central Florida's finest schools, shopping, restaurants, parks, entertainment, businesses and more!
#O6340919

MAITLAND

791 SEQUOIA TRAIL

5 Beds

3 Baths

4,144 Sq.Ft.

$1,199,000

MLS#: O6340919

One or more photo(s) has been virtually staged. NEW PRICE! Discover your private oasis in the heart of Maitland, perfectly tucked away on a quiet cul-de-sac within an exclusive gated enclave of only 19 custom homes. Ideally positioned between Lake Sybelia and Lake Catherine, this one-owner estate blends timeless sophistication, modern comfort, and exceptional livability. With five spacious bedrooms, four-and-a-half baths, and a three-car garage, the home showcases soaring ceilings, elegant architectural details, and an open, flexible layout designed for today’s lifestyle. The gourmet kitchen features solid wood cabinetry, a large island, new refrigerator, walk-in pantry, and dual breakfast bars flowing effortlessly into the formal dining and family rooms, where a cozy gas fireplace and custom wet bar create the perfect space for entertaining. Thoughtfully designed for multigenerational living, the residence includes two private wings—one featuring a complete in-law suite with full kitchen, expansive living area, bedroom, bath, and private entrance. Upstairs, the luxurious owner’s retreat offers a loft-style office and sitting area, dual walk-in closets, and a spa-inspired bath. Step outside to a lush tropical paradise where a sparkling saltwater pool with new equipment, papaya trees, and blooming amaryllis create a serene, resort-style ambiance. Additional highlights include a new roof (2023), first-floor laundry with newer appliances, tray ceilings, archways, and low HOA fees. Just minutes from top-rated schools, parks, restaurants, Park Avenue, Hannibal Square and the Winter Park Village, with scenic walkability or a bike ride along Lake Sybelia to local cafés, the Sunday Farmers Market, and the Maitland Art Museum, this exquisite home offers the rare combination of privacy, sophistication, and convenience in one of Central Florida’s most sought-after communities. Schedule your private showing today and experience the extraordinary lifestyle this Maitland masterpiece provides.
#O6299581

MAITLAND

755 CRANES COURT

5 Beds

4 Baths

4,566 Sq.Ft.

$1,419,000

MLS#: O6299581

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service