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Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of modern amenities. From the moment you arrive, the wraparound porch and circular drive create a welcoming first impression, setting the tone for the timeless character found throughout. Step inside to a gracious foyer accented by a cozy fireplace, leading into the spacious formal living room with its own gas fireplace and the elegant formal dining room. Gorgeous heart-of-pine floors run throughout the first floor, adding warmth and authenticity. The kitchen has been thoughtfully updated with top-of-the-line Thermador and Sub-Zero appliances, including a 72-bottle Sub-Zero wine tower and refrigerated drawers, making it as functional as it is beautiful. Open to the family room, complete with rich woodwork and a third gas fireplace, this space is ideal for gathering and entertaining. The primary suite is conveniently located on the first floor and features an updated ensuite bath. Upstairs, three additional bedrooms and two renovated baths provide comfortable accommodations for family and guests. A charming "sleeping room," now used as a light-filled office, overlooks picturesque New England Avenue. Adding to the property's appeal is a detached two-story guest house offering a full bedroom, full bath, sitting area, and kitchen"”perfect for extended stays or as a private retreat. Outdoor living is equally inviting, with a back porch for grilling, a separate patio for lounging and mature landscaping that enhances the home's curb appeal. Architectural details available for adding an oversize two-car garage, if desired. Perfectly positioned on the same block as The Alfond Inn and just two short blocks from the renowned Park Avenue district, this home offers not just refined living, but a downtown walkable lifestyle that is truly unmatched. Park Avenue is the cultural heart of Winter Park"”a tree-lined promenade alive with award-winning restaurants, boutique shopping, art galleries and historic landmarks. Residents enjoy a vibrant calendar of events, from the Winter Park Farmers' Market and seasonal art festivals to beloved holiday parades and outdoor movies under the stars. Here, every day is an invitation to experience the best of Central Florida living"”whether it's sipping coffee at a charming café, strolling to or after dinner surrounded by beautiful ambience, or embracing the timeless traditions that make Winter Park so treasured.
| DAYS ON MARKET | 156 | LAST UPDATED | 11/10/2025 |
|---|---|---|---|
| TRACT | WINTER PARK | YEAR BUILT | 1920 |
| COMMUNITY | 32789 - Winter Park | COUNTY | Orange |
| STATUS | Active | PROPERTY TYPE(S) | Single Family |
| Elementary School | Audubon Park K8 |
|---|---|
| Jr. High School | Audubon Park K-8 |
| High School | Winter Park High |
| ADDITIONAL DETAILS | |
| AIR | Central Air, Zoned |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator |
| AREA | 32789 - Winter Park |
| BASEMENT | Crawl Space |
| CONSTRUCTION | Frame, Vinyl Siding |
| EXTERIOR | Rain Gutters |
| FIREPLACE | Yes |
| HEAT | Central, Zoned |
| INTERIOR | Crown Molding, Eat-in Kitchen, High Ceilings, Stone Counters |
| LOT | 0.41 acre(s) |
| LOT DESCRIPTION | Corner Lot, Landscaped, Level |
| LOT DIMENSIONS | 120 x 170 x 88 x 182 |
| PARKING | Circular Driveway, Driveway, Parking Pad |
| SEWER | Public Sewer |
| STORIES | 2 |
| STYLE | Traditional |
| SUBDIVISION | WINTER PARK |
| TAXES | 3875.98 |
| UTILITIES | Natural Gas Available, Natural Gas Connected, Underground Utilities |
| WATER | Public |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listing provided by Mick Night, PREMIER SOTHEBY'S INTL. REALTY, 407-644-3295
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 2/28/26 2:03 PM PST.
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