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Canal Front Oasis on the Winter Park Chain of Lakes! Welcome to 1016 Howell Branch Road, where every day feels like a getaway. 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.) 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. With no HOA, residents may optionally join the neighborhood association (approx. $120/year) for access to two lakefront parks and a private boat ramp. 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.
| DAYS ON MARKET | 0 | LAST UPDATED | 2/27/2026 |
|---|---|---|---|
| TRACT | MAITLAND SHORES | YEAR BUILT | 1959 |
| COMMUNITY | 32789 - Winter Park | GARAGE SPACES | 2.0 |
| COUNTY | Orange | STATUS | Active |
| PROPERTY TYPE(S) | Single Family |
| Elementary School | Dommerich Elem |
|---|---|
| Jr. High School | Maitland Middle |
| High School | Winter Park High |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Dishwasher, Disposal, Exhaust Fan, Freezer, Range, Range Hood, Refrigerator |
| AREA | 32789 - Winter Park |
| CONSTRUCTION | Block, Frame |
| EXTERIOR | Dock, Lighting, Private Yard, Rain Gutters |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Central, Electric, Heat Pump |
| INTERIOR | Built-in Features, Crown Molding, Dry Bar, Eat-in Kitchen, High Ceilings, Open Floorplan, Smart Home, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s) |
| LOT | 0.37 acre(s) |
| LOT DESCRIPTION | Waterfront |
| PARKING | Attached |
| SEWER | Public Sewer |
| STORIES | 2 |
| SUBDIVISION | MAITLAND SHORES |
| TAXES | 9074 |
| UTILITIES | Cable Available, Electricity Connected, Propane, Sewer Connected, Underground Utilities, Water Connected |
| VIEW | Yes |
| VIEW DESCRIPTION | Canal, Water, Trees/Woods |
| WATER | Public |
| WATER ACCESS | HOWELL CREEK, LAKE MAITLAND |
| WATERFRONT | Yes |
| WATERFRONT DESCRIPTION | Canal Front, Lake Privileges |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listing provided by Andrew Birr, PLAID PROPERTIES, LLC, 407-702-0864
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 2/27/26 11:38 AM PST.
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