Gabriella Massaro

Gabriella Massaro Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

$7,200.00/month
1016 HOWELL BRANCH ROAD, WINTER PARK, FL - 32789
4 beds
3.0 baths
3,142 sqft
$7,200.00/month
1016 HOWELL BRANCH ROAD, WINTER PARK, FL - 32789
Gabriella Massaro
$7,200.00/month
4 beds
3.0 baths
3,142 sqft
1016 HOWELL BRANCH ROAD, WINTER PARK, FL - 32789
For Rent
Photo 1
  • Built in 1959
  • 2 garage spaces
  • Lot size: 16,235 sqft

Canal Front Oasis on the Winter Park Chain of Lakes! Welcome to 1016 Howell Branch Road, where every day feels like a getaway. (Property can be leased furnished for an additional fee.) This beautifully reimagined 4-bedroom, 3-bath residence offers 3,142 square feet of inspired living space set amid lush, tropical landscaping — all within the best of Winter Park and Maitland. *The canal allows for full Lake Maitland and Winter Park Chain of Lakes access by powerboat. (Current owners have a 19' outboard they use to pull tubes, ski, wakeboard, quick trips to dog island and entertaining via scenic tours through the Winter Park Chain of Lakes. Bring your own boat / kayaks and enjoy. (An outboard boat is recommended as the canal depth varies.) Originally built in 1959 and completely renovated in 2022, this two-story retreat combines rustic charm with modern luxury. Step inside to discover an open floor plan anchored by a gas fireplace, open kitchen and dining room, warm custom woodwork, and thoughtful built-ins throughout. The renovation includes new electrical, plumbing, new kitchen and baths, engineered hardwood flooring throughout, amongst many more upgrades. The redesigned layout adds over 1,000 square feet, featuring a spacious first-floor laundry room and an all-new second story with a luxurious primary suite, a guest bedroom (currently used as an office), and a full bathroom. Outdoors, enjoy a new boathouse on a canal and an inviting outdoor living area — perfect for entertaining or unwinding along the peaceful canal that connects directly to Lake Maitland and the renowned Winter Park Chain of Lakes. The rear of the property backs up to a wooded conservation area that provides privacy and tranquility. The current owner received a variance for a future pool, and Orange County previously had no objections to pool installation (new owner would need to reapply). The property sits in one of Central Florida’s most sought-after school zones: Dommerich Elementary, Maitland Middle, and Winter Park High. Families here often bike or walk to school. Enjoy regular walks through scenic streets lined with mature cypress trees, palms, vibrant native vegetation and beautiful homes that line Lake Maitland. From the modern amenities and artful landscaping to the serene waterfront setting, this is truly a one-of-a-kind property that blends nature, comfort, and sophistication in the heart of Winter Park. *Canal boat tour video that showcases the trip from the canal to Lake Maitland is available via the virtual tour link in the listing.

  • Directions: From Kings Row Park head east on Howell Branch Rd. Property is the 3rd house on the right. Property is not on the main "Howell Branch Rd." The main road veers off into a residential neighborhood where the house is located.
  • County: Orange
  • Geo subdivision: MAITLAND SHORES

Nearby Schools

Dommerich Elem

Maitland Middle

Winter Park High

Features

Financial

Let's get in touch!

Gabriella Massaro

Gabriella Massaro

Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

See also

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2075 JEWELL AVENUE, WINTER PARK, FL - 32789
$6,995.00
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Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6392422
Listing updated: March 21, 2026 at 5:00AM
Listing provided by: Andrew Birr, PLAID PROPERTIES, LLC
Last checked 4 days ago
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